Five-Membered Hetarynes

  • Manfred G. Reinecke

Abstract

Concepts as well as matter exhibit the property of inertia. Truly new concepts meet an initial resistance proportional to their novelty, which, if it is overcome, converts to a powerful force directed at extending the idea far beyond its original sphere of applicability and appropriateness. Science is no less subject to this generalization than are the social sciences and humanities but has the obvious advantage of permitting—or rather requiring—the constant testing of its concepts against experimental fact. One of the best illustrations of such intellectual inertia in chemistry is found in the concept of reactive intermediates. Free radicals, carbanions, carbenes, and carbenium ions have all gone through this cycle of postulation, proof, overextension, and retrenchment. The consequences of this process are such modifications as radicaloids, complexed carbanions, carbenoids, and the “nonclassical ion problem.” The concept of the aryne intermediate has also followed this path albeit more recently and with less fanfare than some of its relatives. A central role in both the overextension and maturing of the aryne concept is played by five-membered hetarynes. It is the purpose of this chapter to critically examine this role through a detailed review of the postulation, preparation, and properties of five-membered hetarynes.

Keywords

Quinone Dehydrogenation Piperidine Triphenylene Thiadiazole 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References and Notes

  1. 1.
    T. Kaufmann, Angew. Chem. Int. Ed. Engl. 4, 543 (1965).Google Scholar
  2. 2.
    H. J. den Hertog and H. C. van der Pias, Adv. Heterocycl. Chem. 4, 121 (1965).Google Scholar
  3. 3.
    H. J. den Hertog and H. C. van der Pias, in Chemistry of Acetylenes, H. G. Viehe, Ed., Marcel Dekker, New York (1969), Chap. 17, p. 1149–1197.Google Scholar
  4. 4.
    T. Kauffmann and R. Wirthwein,Angew. Chem. Int. Ed. Engl. 10, 20 (1971).Google Scholar
  5. 5.
    R. W. Hoffmann,Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967).Google Scholar
  6. 6.
    R. Huisgen, inOrganometallic Chemistry, H. Zeiss, Ed., Reinhold, New York (1960), p. 36–87.Google Scholar
  7. 7.
    J. F. Bunnett, J. Chem. Educ. 38, 278 (1961);Google Scholar
  8. H. Heaney, Chem. Rev. 62, 81 (1962);Google Scholar
  9. W. Czuba, Wiad. Chem. 19, 157 (1965).Google Scholar
  10. 8.
    S. M. A. Hai and A. W. Qureshi, Pak. J. Sci. Ind. Res. 17, 65 (1974);Google Scholar
  11. O. M. Nefedov, A. I. Dyachenko, and A. K. Prokofev, Russ. Chem. Rev. 46, 941 (1977).ADSGoogle Scholar
  12. 9.
    G. Wittig, Angew. Chem. Int. Ed. Engl. 4, 731 (1965).Google Scholar
  13. 10.
    R. W. Hoffmann, in Chemistry of Acetylenes, H. G. Viehe, Ed., Marcel Dekker, New York (1969), Chap. 16, p. 1063–1148.Google Scholar
  14. 11.
    E. K. Fields, in Organic Reactive Intermediates, S. P. McManus, Ed., Academic Press, New York (1973), Chap. 7, p. 449–508.Google Scholar
  15. 11a.
    Two additional reviews on hetarynes have been written since this manuscript was completed. The first deals with all hetarynes; M. G. Reinecke, Tetrahedron, 38, in press (1982). The second covers six-membered hetarynes only; H. C. van der Pias, in The Chemistry of Triple Bonded Groups, Supplement C of the Chemistry of the Functional Groups, S. Patai and Z. Rappoport, Eds., Wiley-Interscience, New York (1982).Google Scholar
  16. 12.
    J. D. Roberts, D. A. Semenow, H. E. Simmons, Jr., and L. A. Carlsmith, J. Am. Chem. Soc. 78, 601 (1956).Google Scholar
  17. 13(a).
    W. N. Washburn,J. Am. Chem. Soc. 97, 1615 (1975);Google Scholar
  18. (b).
    R. Breslow, J. Napierski, and T. C. Clarke, J. Am. Chem. Soc. 97, 6275 (1975).Google Scholar
  19. 14.
    J. D. Roberts, H. E. Simmons, Jr., L. A. Carlsmith, and C. W. Vaughn, J. Am. Chem. Soc. 75, 3290 (1953).Google Scholar
  20. 15.
    G. Wittig, Naturwissenschaften 30, 696 (1942).ADSGoogle Scholar
  21. 16.
    T. Kauffmann, F. P. Boettcher, and J. Hansen,Angew. Chem. 73, 341 (1961).Google Scholar
  22. 17.
    R. Levine and W. W. Leake, Science 121, 780 (1955).ADSGoogle Scholar
  23. 18.
    D. A. de Bie, H. C. van der Pias, and G. Geursten, Ree. Trav. Chim. Pays-Bas 90, 594 (1971).Google Scholar
  24. 19.
    W. Adam, A. Grimison, and R. Hoffmann, J. Am. Chem. Soc. 91, 2590 (1969).Google Scholar
  25. 20.
    R. D. Hamilton and E. Campaigne, in Special Topics in Heterocyclic Chemistry, A. Weissberger and E. C. Taylor, Eds., Wiley-Interscience, New York (1977), p. 271.Google Scholar
  26. 21.
    H. L. Jones and D. L. Beveridge, Tetrahedron Lett., 1577 (1964).Google Scholar
  27. 22.
    N. N. Zatsepina and I. F. Tupitsyn, Chem. Heterocycl. Comp. (USSR) 10, 1397 (1974).Google Scholar
  28. 23.
    A. Streitwieser and P. J. Scannon, J. Am. Chem. Soc. 95, 6273 (1973).Google Scholar
  29. 24.
    J. A. Zoltewicz, G. Grahe, and C. L. Smith, J. Am. Chem. Soc. 91, 5501 (1969);Google Scholar
  30. R. A. Abramovitch, I. M. Singer, and A. R. Vinutha,Chem. Commun., 55 (1967).Google Scholar
  31. 25.
    W. G. Salmond, Q. Rev. Chem. Soc. 22, 253 (1968).Google Scholar
  32. 26.
    R. F. Heldweg and H. Hogeveen, Tetrahedron Lett., 75 (1974).Google Scholar
  33. 27.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes. Academic Press, New York (1967), p. 275.Google Scholar
  34. 28.
    F. Bernardi, I. G. Csizmadia, A. Mangini, H. B. Schlegel, M. H. Whangbo, and S. Wolfe, J. Am. Chem. Soc. 97, 2209 (1975).Google Scholar
  35. 29.
    R. A. Olofson, J. M. Landesberg, K. N. Houk, and J. S. Michelman, J. Am. Chem. Soc. 88, 4265 (1966).Google Scholar
  36. 30.
    P. Haake, L. P. Bausher, and W. B. Miller, J. Am. Chem. Soc. 91, 1113 (1969).Google Scholar
  37. 31.
    P. Haake, L. P. Bausher, and W. B. Miller, J. Am. Chem. Soc. 91, 1113 (1969), footnote 39.Google Scholar
  38. 32.
    F. G. Bordwell, M. van der Puy, and N. R. Vanier, J. Org. Chem. 41, 1885 (1976).Google Scholar
  39. 33.
    A. Streitwieser and S. P. Ewing, J. Am. Chem. Soc. 97, 190 (1975).Google Scholar
  40. 34.
    J. A. Elvidge, J. R. Jones, C. O’Brien, E. A. Evans, and H. C. Sheppard, Adv. Heterocycl. Chem. 16, 1 (1974).Google Scholar
  41. 35.
    M. Berthelot, Justus Liebigs Ann. Chem. 142, 251 (1867).Google Scholar
  42. 36.
    C. deMilt, J. Chem. Ed. 28, 421 (1951).Google Scholar
  43. 37.
    E. Dreher and R. Otto, Justus Liebigs Ann. Chem. 154, 93 (1870).Google Scholar
  44. 38.
    R. Stoermer and B. Kahlert, Chem. Ber. 35, 1633 (1902).Google Scholar
  45. 39.
    O. Diels and M. Reinbeck,Chem. Ber. 43, 1271 (1910).Google Scholar
  46. 40.
    A. Michael, Chem. Ber. 39, 1915 (1906).Google Scholar
  47. 41.
    E. Ott, Chem. Ber. 47, 2388 (1914).Google Scholar
  48. 42.
    W. E. Bachman and H. T. Clarke, J. Am. Chem. Soc. 49, 2089 (1927).Google Scholar
  49. 43.
    A. Luttringhaus and G. V. Sääf, Justus Liebigs Ann. Chem. 542, 241 (1939).Google Scholar
  50. 44.
    A. A. Morton, J. B. Davidson, and B. L. Hakan, J. Am. Chem. Soc. 64, 2242 (1942).Google Scholar
  51. 45.
    G. Wittig and G. Fuhrmann, Chem. Ber. 73, 1197 (1940).Google Scholar
  52. 46.
    R. Huisgen and H. Rist, Naturwissenschaften 41, 358 (1954);ADSGoogle Scholar
  53. R. Huisgen and H. Rist, Justus Liebigs Ann. Chem. 594, 137 (1955).Google Scholar
  54. 47.
    G. Wittig and L. Pohmer, Chem. Ber. 89, 1334 (1956).Google Scholar
  55. 48.
    M. Stiles, R. G. Miller, and U. Burckhardt,J. Am. Chem. Soc. 85, 1792 (1963).Google Scholar
  56. 49.
    G. Wittig and R. W. Hoffmann, Chem. Ber. 95, 2718 (1962).Google Scholar
  57. 50.
    C. D. Campbell and C. W. Rees, J. Chem. Soc. C, 742 (1969).Google Scholar
  58. G. Wittig, Pure Appl. Chem. 7, 173 (1963).Google Scholar
  59. R. S. Berry, G. N. Spokes, and M. Stiles, J. Am. Chem. Soc. 84, 3570 (1962).Google Scholar
  60. G. Wittig and H. F. Ebel, Justus Liebigs Ann. Chem. 650, 20 (1961).Google Scholar
  61. R. S. Berry, J. Clardy, and M. E. Schafer, J. Am. Chem. Soc. 86, 2738 (1964).Google Scholar
  62. R. Husigen and R. Knorr, Tetrahedron Lett., 1017 (1963).Google Scholar
  63. B. H. Klanderman and T. R. Criswell, J. Am. Chem. Soc. 91, 510 (1969).Google Scholar
  64. O. L. Chapman, K. Mattes, C. L. Mcintosh, J. Pacansky, G. V. Calder, and G. Orr, J. Am. Chem. Soc. 95, 6134 (1973).Google Scholar
  65. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), Chapt. 5.Google Scholar
  66. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes. Academic Press, New York (1967), Chapt. 6.Google Scholar
  67. L. B. Dashkevich, V. A. Buevich, and B. E. Kubaev, J. Gen. Chem. USSR 30, 1925 (1960).Google Scholar
  68. G. Wittig and V. Wahl, Angew. Chem. 73, 492 (1961).Google Scholar
  69. G. Wittig, Angew. Chem. Int. Ed. Engl. 1, 415 (1962).Google Scholar
  70. G. Komppa and S. Weckman, J. Prakt. Chem. 138, 109 (1933).Google Scholar
  71. F. G. Bordwell, B. B. Lampert, and W. H. McKellin, J. Am. Chem. Soc. 71, 1702 (1949).Google Scholar
  72. K. R. Brower and E. D. Amstutz, J. Org. Chem. 19, 411 (1954).Google Scholar
  73. T. Kauffmann and F. P. Boettcher, Chem. Ber. 95, 949 (1962).Google Scholar
  74. T. Kauffmann, A. Risberg, J. Schulz, and R. Weber, Tetrahedron Lett., 3563 (1964).Google Scholar
  75. T. Kauffmann, R. Nürnberg, J. Schulz, and R. Stobba, Tetrahedron Lett., 4273 (1967).Google Scholar
  76. R. Fusco and M. Bianchi, Gazz. Chim. Ital. 97, 410 (1967).Google Scholar
  77. W. Draber, Angew. Chem. Int. Ed. Engl. 6, 75 (1967).Google Scholar
  78. E. K. Fields and S. Meyerson, Chem. Commun., 708 (1966).Google Scholar
  79. E. K. Fields and S. Meyerson, in Organosulfur Chemistry, M. J. Janssen, Ed., Interscience Publishers, New York (1967), p. 143.Google Scholar
  80. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 293.Google Scholar
  81. L. Crombie, P. A. Gilbert, and R. P. Houghton, Chem. Commun., 595 (1967).Google Scholar
  82. M. G. Reinecke and H. W. Adickes, J. Am. Chem. Soc. 90, 511 (1968).Google Scholar
  83. G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  84. M. G. Reinecke and J. G. Newson, J. Am. Chem. Soc. 98, 3021 (1976);Google Scholar
  85. M. G. Reinecke, J. G. Newsom, and L. J. Chen, J. Am. Chem. Soc. 103, 2760 (1981).Google Scholar
  86. H. Ballard, unpublished results, Texas Christian University (1977).Google Scholar
  87. M. G. Reinecke and H. Ballard, Tetrahedron Lett., 4981 (1979).Google Scholar
  88. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 9–31.Google Scholar
  89. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 43–58; (b)pp. 32–42.Google Scholar
  90. R. F. Cunico and E. M. Dexheimer, J. Organometal. Chem. 59, 153 (1973).Google Scholar
  91. J. F. Bunnett and B. F. Hrutfiord, J. Org. Chem. 27, 4152 (1962).Google Scholar
  92. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 37–41.Google Scholar
  93. E. McNelis, J. Org. Chem. 28, 3188 (1963);Google Scholar
  94. G. Köbrich, Justus Liebigs Ann. Chem. 664, 88 (1963).Google Scholar
  95. G. Cainelli, G. Zubiani, and S. Morrocchi, Chim. Ind. (Milan) 46, 1489 (1964);Google Scholar
  96. F. C. Fischer and E. Havinga, Ree. Trav. Chim. Pays-Bas 93, 21 (1974).Google Scholar
  97. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 40.Google Scholar
  98. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 72.Google Scholar
  99. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 37.Google Scholar
  100. F. M. Beringer and S. J. Huang, J. Org. Chem. 29, 445 (1964).Google Scholar
  101. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 238.Google Scholar
  102. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 62–65.Google Scholar
  103. F. L. Scott and R. E. Oesterling, J. Am. Chem. Soc. 82, 5247 (1960).Google Scholar
  104. T. Akiyama, Y. Imasaki, and M. Kawanisi, Chem. Lett., 229 (1974).Google Scholar
  105. J. I. G. Cadogan, A. G. Rowley, J. T. Sharp, B. Sledzinski, and N. H. Wilson, J. Chem. Soc. Perkin Trans. 7, 1072 (1975).Google Scholar
  106. I. Fleming and T. Mah, J. Chem. Soc. Perkin Trans. 1, 1577 (1976).Google Scholar
  107. K. Grohmann, personal communication, cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 66.Google Scholar
  108. H. Meier and K.-P. Zeller, Angew. Chem. Int. Ed. Engl. 16, 835 (1977).Google Scholar
  109. R. W. Hoffmann, Chem. Ber. 98, 222 (1965);Google Scholar
  110. J. F. Bunnett and D. A. R. Happer, J. Org. Chem. 31, 2369 (1966).Google Scholar
  111. H. Zollinger, Acc. Chem. Res. 6, 335 (1973).Google Scholar
  112. H. Zollinger, Angew. Chem. Int. Ed. Engl. 17, 141 (1978),Google Scholar
  113. J. F. Bunnett and C. Yijima, J. Org. Chem. 42, 639 (1977).Google Scholar
  114. L. Friedman and F. M. Logullo, J. Org. Chem. 34, 3089 (1969).Google Scholar
  115. A. Hantzsch and W. B. Davidson, Chem. Ber. 29, 1522 (1896).Google Scholar
  116. F. M. Logullo, dissertation, Case Institute of Technology (1965);Google Scholar
  117. R. M. Roberts, J. C. Gilbert, L. B. Rodewald, and A. S. Wingrove, An Introduction to Modern Experimental Organic Chemistry, Holt, Rinehart and Winston, New York (1969), p. 196–201.Google Scholar
  118. L. Friedman, personal communication, cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 75.Google Scholar
  119. 57.
    J. Nakayama, O. Simamura, and M. Yoshida, J. Chem. Soc. D, 1222 (1970).Google Scholar
  120. 58.
    R. Gompper, E. Kutter, and G. Seybold, Chem. Ber. 101, 2340 (1968).Google Scholar
  121. 59.
    Y. Maki, T. Furuta, M. Kuzuya, and M. Suzuki, J. Chem. Soc. Chem. Commun. 616 (1975).Google Scholar
  122. 60.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 74–77.Google Scholar
  123. 61.
    R. Gompper, G. Seybold, and B. Schmolke, Angew. Chem. Int. Ed. Engl. 7, 389 (1968).Google Scholar
  124. 62.
    S. Yaroslavsky, Chem. Ind. (London), 765 (1965).Google Scholar
  125. 63.
    D. C. Dittmer and E. S. Whitman, J. Org. Chem. 34, 2004 (1969).Google Scholar
  126. 64.
    H. Heaney, J. M. Japlonski, and C. T. McCarty, J. Chem. Soc. Perkin Trans, 1, 2903 (1972);Google Scholar
  127. J. M. Rao and S. Mallikarjuna, Tetrahedron Lett., 283 (1979).Google Scholar
  128. 65.
    N. Dennis, A. R. Katritzky, and S. K. Parton, J. Chem. Soc. Perkin Trans, h 750 (1974).Google Scholar
  129. The zwitterion 36 generated from 321 apparently adds to benzyne (1) to give benzcoumarin,90 a product which has not been observed in reactions of 41a.117 Google Scholar
  130. 67.
    L. Friedman and M. Stiles, personal communications cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 238.Google Scholar
  131. 68.
    T. J. Barton, A. J. Nelson, and J. Clardy, J{ø Org. Chem. 37, 895 (1972).Google Scholar
  132. 69.
    S. Yaroslavsky, Tetrahedron Lett., 1503 (1965).Google Scholar
  133. 70.
    R. J. Osiewicz, Dissertation, Case Western Reserve University (1972).Google Scholar
  134. 71.
    O. L. Chapman, C. L. Mcintosh, J. Pecansky, G. V. Calder, and G. Orr, J. Am. Chem. Soc. 95, 4061 (1973).Google Scholar
  135. 72.
    S. F. Dyke, A. J. Floyd, and S. E. Ward, Tetrahedron 26, 4005 (1970).Google Scholar
  136. 73.
    R. R. Schmidt and W. Schneider, Tetrahedron Lett., 5095 (1970).Google Scholar
  137. 74.
    R. A. Rossi, R. H. de Rossi, and H. E. Bertorello, J. Org. Chem. 36, 2905 (1971).Google Scholar
  138. 75.
    R. Ghosh, E. B. Sheinin, C. L. Bell, and L. Bauer, J. Heterocycl. Chem. 12, 203 (1975).Google Scholar
  139. 76.
    J. I. G. Cadogan, Acc. Chem. Res. 4, 186 (1971).Google Scholar
  140. 77.
    P. C. Buxton and H. Heaney, J. Chem. Soc. Chem. Commun., 545 (1973).Google Scholar
  141. 78.
    J. I. G. Cadogan, C. D. Murray, and J. T. Sharp, J. Chem. Soc. Perkin Trans. 1, 1321 (1974).Google Scholar
  142. 79.
    (a) D. L. Brydon, J. I. G. Cadogan, J. Cook, M. J. P. Harger, and J. T. Sharp, J. Chem. Soc. B., 1996 (1971);Google Scholar
  143. J. I. G. Cadogan, D. M. Smith, and J. B. Thomson, Chem. Soc. Perkin Trans. 1, 1296 (1972).Google Scholar
  144. 80.
    B. Baigrie, J. I. G. Cadogan, J. R. Mitchell, A. K. Robertson, and J. T. Sharp, J. Chem. Soc. Perkin Trans. 1, 2563 (1972).Google Scholar
  145. 81.
    C. Ruchardt and C. C. Tan, Chem. Ber. 103, 1774 (1970).Google Scholar
  146. 82.
    J. I. G. Cadogan, C. D. Murray, and J. T. Sharp, J. Chem. Soc. Perkin Trans. 2, 583 (1976).Google Scholar
  147. 83.
    C. Rùchardt and C. C. Tan, Angew. Chem. Int. Ed. Engl. 9, 522 (1970).Google Scholar
  148. 84.
    H. Teichmann, M. Jatkowski, and G. Hilgetag, Prakt. Chem. 314, 129 (1972).Google Scholar
  149. 85.
    M. Kato, T. Tamano, and T. Miwa, Bull. Chem. Soc. Jap. 48, 291 (1975).Google Scholar
  150. 86.
    T. E. Stevens, J. Org. Chem. 33, 855 (1968).Google Scholar
  151. 87.
    E. A. Dorko and T. E. Stevens, Chem. Commun., 871 (1966).Google Scholar
  152. 88.
    (a) J. A. Kampmeier and A. B. Rubin, Tetrahedron Lett., 2853 (1966);Google Scholar
  153. D. L. Brydon and J. I. G. Cadogan, J. Chem. Soc. C, 819 (1968).Google Scholar
  154. B. H. Klanderman, D. P. Maier, G. W. Clark, and J. A. Kampmeier, J. Chem. Soc. D, 1003 (1971).Google Scholar
  155. 90.
    G. W. Clark and J. A. Kampmeier, Chem. Soc. D, 996 (1970).Google Scholar
  156. 91.
    L. Verbit, J. S. Levy, H. Rabitz, and W. Kwalwasser, Tetrahedron Lett., 1053 (1966).Google Scholar
  157. 92.
    R. A. Abramovitch and G. N. Knaus, J. Org. Chem. 40, 883 (1975).Google Scholar
  158. 93.
    A. Hantzsch and R. Glogauer, Chem. Ber. 30, 2548 (1897).Google Scholar
  159. 94.
    M. Stiles and R. G. Miller, J. Am. Chem. Soc. 82, 3802 (1960).Google Scholar
  160. 95.
    R. W. Hoffmann, W. Sieber, and G. Guhn, Chem. Ber. 98, 3470 (1965).Google Scholar
  161. 96.
    K. Ramanathan, dissertation, University of Rochester (1974); Diss. Abstr. Int. B 36, 243 (1975).Google Scholar
  162. 97.
    V. Franzen and H.-I. Joschek, Justus Liebigs Ann. Chem. 703, 90 (1967).Google Scholar
  163. 98.
    R. W. Hoffmann and W. Sieber, Justus Liebigs Ann. Chem. 703, 96 (1967).Google Scholar
  164. 99.
    A. T. Fanning, Jr. and T. D. Roberts, Tetrahedron Lett., 805 (1971).Google Scholar
  165. 100.
    A. T. Fanning, Jr., G. R. Bickford, and T. D. Roberts, J. Am. Chem. Soc. 94, 8505 (1972).Google Scholar
  166. 101.
    B. M. Adger, M. Keating, C. W. Rees, and R. C. Storr, J. Chem. Soc. Perkin Trans. 1, 41 (1975).Google Scholar
  167. 102.
    N. Bashir and T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1, 868 (1973).Google Scholar
  168. 103.
    M. S. Ao, E. M. Burgess, A. Schauer, and E. A. Taylor, Chem. Commun., 220 (1969).Google Scholar
  169. 104.
    J. Adamson, D. L. Forster, T. L. Gilchrist, and C. W. Rees, Chem. Commun., 221 (1969).Google Scholar
  170. 105.
    J. Adamson, D. L. Forster, T. L. Gilchrist, and C. W. Rees, J. Chem. Soc. C, 981 (1971).Google Scholar
  171. 106.
    E. F. Ullman and E. A. Bartkus, Chem. Ind. (London)., 93 (1962).Google Scholar
  172. 107.
    D. L. Forster, T. L. Gilchrist, C. W. Rees, and E. Stanton, J. Chem. Soc. D, 695 (1971).Google Scholar
  173. 108.
    (a) C. D. Campbell and C. W. Rees, Chem. Soc. C, 752 (1969);Google Scholar
  174. C. W. Rees and R. C. Storr, Chem. Commun., 1305 (1968).Google Scholar
  175. 109.
    J. I. G. Cadogan and J. B. Thomson, Chem. Commun., 770 (1969).Google Scholar
  176. 110.
    M. Keating, M. E. Peek, C. W. Rees, and R. C. Storr, J. Chem. Soc. Perkin Trns. 1, 1315 (1972).Google Scholar
  177. 161.
    C. W. Rees, personal communication, cited by R. W. Hoffman in Chemistry of Acetylenes, H. G. Viehe, Ed., Marcel Dekker, New York (1969), Chap. 16, p. 1091.Google Scholar
  178. 162.
    B. M. Adger, S. Bradbury, M. Keating, C. W. Rees, R. C. Storr, and M. T. Williams, J. Chem. Soc. Perkin Trans. 1, 31 (1975).Google Scholar
  179. 163.
    O. L. Chapman, C.-C. Chang, J. Kole, N. R. Rosenquist, and H. Tomioka, J. Am. Chem. Soc. 97, 6586 (1975).Google Scholar
  180. 164.
    G. Ege and G. Jooss, Chem. Ber. 106, 1978 (1973).Google Scholar
  181. 165.
    R. S. Atkinson and C. W. Rees, Chem. Commun., 1230 (1967).Google Scholar
  182. 166.
    J. D. White and M. Kim, Tetrahedron Lett., 3361 (1974).Google Scholar
  183. 167.
    J. Fout, M. Torres, H. E. Gunning, and O. P. Strausz, J. Org. Chem. 43, 2487 (1978).Google Scholar
  184. 168.
    I. Lalezari, A. Shafîee, and M. Yalpani, J. Org. Chem. 36, 2836 (1971).Google Scholar
  185. 169.
    M. Torres, A. Clement, J. E. Bertie, H. E. Gunning, and O. P. Strausz, J. Org. Chem. 43, 2490 (1978).Google Scholar
  186. 170.
    N. P. Buu-Hoi, P. Jacquignon, and M. Mangane, Chem. Commun., 624 (1965).Google Scholar
  187. 171.
    C. L. Pederson and J. Moller, Acta Chem. Scand. 29B, 483 (1975).Google Scholar
  188. 172.
    (a) M. Jones, Jr. and M. R. DeCamp, J. Org. Chem. 36, 1536 (1971);Google Scholar
  189. (b).
    R. T. Luibrand and R. W. Hoffmann, J. Org. Chem. 39, 3887 (1974).Google Scholar
  190. 173.
    G. A. Russell, V. Malatesta, D. E. Lawson, and R. Steg, J. Org. Chem., 43, 2242 (1978).Google Scholar
  191. 174.
    F. D. Greene, J. Am. Chem. Soc. 78, 2246 (1956).Google Scholar
  192. 175.
    E. K. Fields and S. Meyerson, Chem. Commun., 474 (1965).Google Scholar
  193. 176.
    R. F. C. Brown, D. V. Gardner, J. F. W. McOmie, and R. K. Solly, Chem. Commun., 407 (1966).Google Scholar
  194. M. P. Cava, M. J. Mitchell, D. C. DeJongh, and R. Y. Van Fossen, Tetrahedron Lett., 2947 (1966).Google Scholar
  195. 178.
    E. K. Fields and S. Meyerson, J. Org. Chem. 31, 3307 (1966).Google Scholar
  196. R. F. C. Brown, D. V. Gardner, J. F. W. McOmie, and R. K. Solly, Aust. J. Chem. 20, 139 (1967).Google Scholar
  197. 180.
    (a) V. E. Platonov, T. V. Senchenko, and G. G. Yakobson, J. Org. Chem. USSR 12, 816 (1976);Google Scholar
  198. (b).
    T. V. Senchenko, V. E. Platonov, and G. G. Yakobson, Org. Chem. USSR 13, 1904 (1977).Google Scholar
  199. 181.
    A. Martineau and D. C. DeJongh, Can. J. Chem. 55, 34 (1977).Google Scholar
  200. 182.
    H. Suhr and A. Szabo, Justus Liebigs Ann. Chem. 752, 37 (1971).Google Scholar
  201. 183.
    G. Porter and J. I. Steinfeld, J. Chem. Soc. A. 877 (1968);Google Scholar
  202. J. Lohmann, J. Chem. Soc. Faraday Trans. 1 68, 814 (1972).Google Scholar
  203. 184.
    I. R. Dunkin and J. G. MacDonald, J. Chem. Soc. Chem. Commun., 772 (1979).Google Scholar
  204. 185.
    S. Meyerson, Ree. Chem. Prog. 26, 257 (1965).Google Scholar
  205. 186.
    H.-F. Grützmacher and J. Lohmann, Justus Liebigs Ann. Chem. 733, 88 (1970).Google Scholar
  206. 187.
    H.-F. Grützmacher and J. Lohmann, Justus Liebigs Ann. Chem. 726, 47 (1969).Google Scholar
  207. 188.
    S. Meyerson and E. K. Fields, Chem. Commun., 275 (1966).Google Scholar
  208. 189.
    M. P. Cava and M. J. Mitchell, Cyclobutadine and Related Compounds, Academic Press, New York (1967), p. 225;Google Scholar
  209. M. P. Cava, personal communication, cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 84.Google Scholar
  210. 190.
    A. Szabo, H. Suhr, and M. Venugopalan, Justus Liebigs Ann. Chem. 747 (1977).Google Scholar
  211. 191.
    (a) R. F. C. Brown and R. K. Solly, Chem. Ind. (London), 181 (1965);Google Scholar
  212. (b).
    R. F. C. Brown and R. K. Solly, Chem. Ind. (London), 1462 (1965);Google Scholar
  213. R. F. C. Brown and R. K. Solly, Aust. J. Chem. 19, 1045 (1966).Google Scholar
  214. 192.
    M. P. David and J. F. W. McOmie, Tetrahedron Lett., 1361 (1973).Google Scholar
  215. 193.
    W. Reichen, Helv. Chim. Acta 60, 186 (1977).Google Scholar
  216. 194.
    J. L. Ripoll, A. Rouessac, and F. Rouessac, Tetrahedron 34, 19 (1978).Google Scholar
  217. 195.
    G. Seybold, Angew. Chem. Int. Ed. Engl. 16, 365 (1977).Google Scholar
  218. 196.
    G. Wittig, H. Härle, E. Knauss, and K. Niethammer, Chem. Ber. 93, 951 (1960).Google Scholar
  219. 197.
    M. Ahmed and J. M. Vernon, J. Chem. Soc. Chem. Commun., 462 (1976).Google Scholar
  220. 198.
    S. J. Cristol and R. Caple, J. Org. Chem. 31, 585 (1966).Google Scholar
  221. 199.
    L. J. Chen, dissertation, Texas Christian University (1978).Google Scholar
  222. 200.
    T. L. Gilchrist, G. E. Gymer, and C. W. Rees, J. Chem. Soc. Perkin Trans. 1, 1747 (1975).Google Scholar
  223. 201.
    L. Friedman and D. F. Lindow, J. Am. Chem. Soc. 90, 2324 (1969).Google Scholar
  224. 202.
    C. E. Griffin and D. C. Wysoeki, J. Org. Chem. 34, 751 (1969).Google Scholar
  225. 203.
    (a) E. J. Corey, F. A. Carey, and R. A. E. Winter, J. Am. Chem. Soc. 87, 934 (1965);Google Scholar
  226. (b).
    E. J. Corey and R. A. E. Winter, Chem. Commun., 208 (1965).Google Scholar
  227. 204.
    E. J. Thomas, J. Chem. Soc. Perkin Trans. 1, 2006 (1973).Google Scholar
  228. 205.
    O. L. Chapman, C. C. Chang, and N. R. Rosenquist, J. Am. Chem. Soc. 98, 261 (1976).Google Scholar
  229. 206.
    S. P. Schmidt and G. B. Schuster, J. Org. Chem. 43, 1823 (1978).Google Scholar
  230. 207.
    R. C. Dougherty, Top. Curr. Chem. 45, 93 (1974).Google Scholar
  231. 208.
    U. E. Wiersum and T. Nieuwenhuis, Tetrahedron Lett., 2581 (1973).Google Scholar
  232. D. C. DeJongh, R. Y. VanFossen, and C. F. Bourgeois, Tetrahedron Lett., 271 (1967).Google Scholar
  233. 210.
    R. A. Abramovitch and S. Wake, J. Chem. Soc. Chem. Commun., 673 (1977).Google Scholar
  234. 211.
    O. L. Chapman and C. L. Mcintosh, J. Am. Chem. Soc. 92, 7001 (1970).Google Scholar
  235. 212.
    O. Tsuge, M. Tashiro, S. Kanemasa, and K. Takasaki, Chem. Lett., 827 (1972).Google Scholar
  236. 213.
    E. Ziegler and H. Sterk, Monatsh. Chem. 99, 1958 (1968).Google Scholar
  237. 214.
    P. DeChamplain, J.-L. Luche, R. A. Marty, and P. DeMayo, Can. J. Chem. 54, 3749 (1976).Google Scholar
  238. 215.
    W. Adam, Angew. Chem. Int. Ed. Engl. 13, 619 (1974).MathSciNetGoogle Scholar
  239. 216.
    (a) P. R. Story, W. H. Morrison, III, T. K. Hall, J.-C. Farine, and C. E. Bishop, Tetrahedron Lett., 3291 (1968);Google Scholar
  240. (b).
    P. R. Story, T. K. Hall, W. H. Morrison, III, and J.-C. Farine, Tetrahedron Lett., 5397 (1968).Google Scholar
  241. 217.
    C. S. Foote, M. T. Wuesthoff, S. Wexler, I. G. Burstain, R. Denny, G. O. Schneck, and K.- H. Schulte-Elte, Tetrahedron 23, 2583 (1967).Google Scholar
  242. 218.
    E. Bernatek and M. Hvatum, Acta Chem. Scand. 14, 836 (1960).Google Scholar
  243. 219.
    H. F. Ebel and R. W. Hoffmann, Justus Liebigs Ann. Chem. 673, 1 (1964).Google Scholar
  244. 220.
    H. Günther, Chem. Ber. 96, 1801 (1963).Google Scholar
  245. 221.
    K. Iqbal and R. C. Wilson, J. Chem. Soc. C, 1690 (1967).Google Scholar
  246. 222.
    I. P. Fisher and F. P. Lossing, J. Am. Chem. Soc. 85, 1018 (1963).Google Scholar
  247. 223.
    J. A. Kampmeier and E. Hoffmeister, J. Am. Chem. Soc. 84, 3787 (1962).Google Scholar
  248. 224.
    N. Kharasch and R. K. Sharma, Chem. Commun., 492 (1967).Google Scholar
  249. 225.
    R. K. Sharma and N. Kharasch, Angew. Chem. Int. Ed. Engl. 7, 36 (1968).Google Scholar
  250. 226.
    J. P. N. Brewer, I. F. Eckhard, H. Heaney, M. G. Johnson, B. A. Marples, and T. J. Ward, J. Chem. Soc. C, 2569 (1970).Google Scholar
  251. 227.
    R. D. Youssefyeh and L. Lictenberg, J. Chem. Soc. Perkin Trans. 1, 2649 (1974).Google Scholar
  252. 228.
    H.-F. Grützmacher and W.-A. Lehman, Justus Liebigs Ann. Chem., 2023 (1975).Google Scholar
  253. 229.
    G. Köbrich, Chem. Ber. 92, 2985 (1959).Google Scholar
  254. 230.
    G. Köbrich and H. Fröhlich, Chem. Ber. 98, 3637 (1965).Google Scholar
  255. 231.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 40–41.Google Scholar
  256. 232.
    H. E. Simmons, J. Org. Chem. 25, 691 (1960).Google Scholar
  257. 233.
    G. Köbrich, Chem. Ber. 96, 2544 (1963).Google Scholar
  258. 234.
    E. K. Fields and S. Meyerson, J. Org. Chem. 41, 916 (1976).Google Scholar
  259. 235.
    B. R. Eggins, Tetrahedron 31, 1191 (1975).Google Scholar
  260. 236.
    P. Sartori and A. Golloch, Chem. Ber. 102, 1765 (1969).Google Scholar
  261. 237.
    E. K. Fields and S. Meyerson, J. Org. Chem. 42, 1691 (1977).Google Scholar
  262. 238.
    P. Sartori and A. Golloch, Chem. Ber. 101, 2004 (1968).Google Scholar
  263. 239.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 77.Google Scholar
  264. 240.
    G. Wittig and F. Bickelhaupt, Chem. Ber. 91, 883 (1958).Google Scholar
  265. 241.
    E. K. Fields and S. Meyerson, J. Am. Chem. Soc. 88, 3388 (1966).Google Scholar
  266. 242.
    E. K. Fields and S. Meyerson, J. Am. Chem. Soc. 89, 3224 (1967).Google Scholar
  267. 243.
    E. K. Fields and S. Meyerson, J. Org. Chem. 32, 3114 (1967).Google Scholar
  268. 244.
    E. K. Fields and S. Meyerson, J. Am. Chem. Soc. 88, 21 (1966).Google Scholar
  269. 245.
    H. Schüler and E. Lutz, Z. Naturforsch. A 16, 57 (1961).ADSGoogle Scholar
  270. 246.
    E. K. Fields and S. Meyerson, Adv. Phys. Org. Chem. 6, 1 (1968).Google Scholar
  271. 247.
    R. A. Abramovitch, J. Roy, and V. Uma, Can. J. Chem. 43, 3407 (1965).Google Scholar
  272. 248.
    R. A. Abramovitch and G. N. Knaus, J. Chem. Soc. Chem. Commun., 238 (1974).Google Scholar
  273. 249.
    E. K. Fields and S. Meyerson, Tetrahedron Lett., 571 (1967).Google Scholar
  274. 250.
    R. R. Jones and R. G. Bergman, J. Am. Chem. Soc. 94, 660 (1972).Google Scholar
  275. 251.
    H.-F. Grützmacher and J. Lohmann, Justus Liebigs Ann. Chem. 705, 81 (1967).Google Scholar
  276. 252.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), Chapt. 2.Google Scholar
  277. 253.
    J. F. Bunnett and R. E. Zahler, Chem. Rev. 49, 273 (1951).Google Scholar
  278. Bunnett and Zahler originally defined a “cine substitution” as one “in which the ring position taken by the entering group is not the same as that vacated by the displaced group.” By usage and convention [V. Gold, Glossary of terms used in physical organic chemistry, Pure Appl. Chem. 51, 1725 (1979)], the term cine has been restricted only to substitution at the position adjacent to the leaving group (previously vicinal cine-substitution) while substitution at positions more remote is referred to as tele-substitution.Google Scholar
  279. 254.
    J. Miller, Nucleophilic Aromatic Substitution, Elsevier Publishing, New York (1968), Chap. 3.Google Scholar
  280. 255.
    J. D. Roberts, C. W. Vaughn, L. A. Carismith, and D. A. Semenov, J. Am. Chem. Soc. 78, 611 (1956).Google Scholar
  281. 256.
    M. Panar and J. D. Roberts, J. Am. Chem. Soc. 82, 3629 (1960).Google Scholar
  282. 257.
    H. J. Shine, Aromatic Rearrangements, Elsevier Publishing, New York (1967), p. 326.Google Scholar
  283. 258.
    J. H. Wotiz and F. Huba, J. Org. Chem. 24, 595 (1959).Google Scholar
  284. 259.
    M. G. Reinecke, Am. Chem. Soc. Div. Petrol. Chem. Preps. 14(2), C68 (1969).Google Scholar
  285. 260.
    M. G. Reinecke, H. W. Adickes, and C. Pyun, J. Org. Chem. 36, 2690 (1971).Google Scholar
  286. 261.
    M. G. Reinecke, H. W. Adickes, and C. Pyun, J. Org. Chem. 36, 3820 (1971).Google Scholar
  287. 262.
    M. G. Reinecke and T. A. Hollingworth, J. Org. Chem. 37, 4257 (1972).Google Scholar
  288. 263.
    H. C. van der Pias, D. A. de Bie, G. Geursten, M. G. Reinecke, and H. W. Adickes, Ree. Trav. Chim. Pays-Bas 93, 33 (1974).Google Scholar
  289. 264.
    D. A. de Bie and H. C. van der Pias, Tetrahedron Lett., 3905 (1968).Google Scholar
  290. 265.
    D. A. de Bie and H. C. van der Pias, Rec. Trav. Chim. Pays-Bas 88, 1246 (1969).Google Scholar
  291. 266.
    D. A. de Bie, H. C. van der Pias, G. Geurtsen, and K. Nijdam, Rec. Trav. Chim. Pays-Bas 92, 245 (1973).Google Scholar
  292. 267.
    J. F. Bunnett, Acc. Chem. Res. 5, 139 (1972).Google Scholar
  293. J. F. Bunnett and C. E. Moyer, Jr., J. Am. Chem. Soc. 92, 1183 (1971), and following papers.Google Scholar
  294. 269.
    R. A. Benkeser and G. Schroll, J. Am. Chem. Soc. 75, 3196 (1953).Google Scholar
  295. 270.
    T. Kauffmann, R. Nürnberg, and K. Udluft, Angew. Chem. Int. Ed. Engl. 7, 617 (1968);Google Scholar
  296. (b).
    T. Kauffmann, R. Nürnberg, and K. Udluft, Chem. Ber. 102, 1177 (1969).Google Scholar
  297. 271.
    S. Senda, K. Hirota, and T. Asao, J. Org. Chem. 40, 353 (1975).Google Scholar
  298. 272.
    G. Guanti, S. Thea, and C. Dell’Erba, Tetrahedron Lett., 461 (1976);Google Scholar
  299. M. Novi, G. Guanti, S. Thea, F. Sancassan, and D. Calabro, Tetrahedron 35, 1783 (1979).Google Scholar
  300. 273.
    D. Bryce-Smith, A. Gilbert, and S. Krestonosich, J. Chem. Soc. Chem. Commun., 405 (1976);Google Scholar
  301. (b).
    R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 2125 (1978);Google Scholar
  302. R. E. Markwell, J. Chem. Soc. Chem. Commun., 428 (1979);Google Scholar
  303. D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc. Chem. Commun., 281 (1980).Google Scholar
  304. 274.
    H. G. Viehe, personal communication quoted in R. W. Hoffmann, in Chemistry of Acetylenes, H. G. Viehe, Ed., Marcel Dekker, New York (1969), Chap. 16, p. 1073.Google Scholar
  305. 275.
    J. A. Zoltewicz, T. M. Oestreich, J. K. O’Halloran, and L. S. Helmick, J. Org. Chem. 38, 1949 (1973).Google Scholar
  306. 276.
    H. C. van der Pias, M. Wozniak, and A. van Veldhuizen, Rec. Trav. Chim. Pays-Bas 96, 151 (1977).Google Scholar
  307. 277.
    A. Albert, Angew. Chem. Int. Ed. Engl. 6, 919 (1967).Google Scholar
  308. 278.
    G. S. Rork and I. H. Pitman, J. Am. Chem. Soc. 97, 5559 (1975);Google Scholar
  309. J. W. Triplett, G. A. Digenis, W. J. Layton, and S. L. Smith, J. Org. Chem. 43, 4411 (1978).Google Scholar
  310. 279.
    J. A. Zoltewicz and J. K. O’Halloran, J. Am. Chem. Soc. 97, 5531 (1975).Google Scholar
  311. 280.
    G. S. Rork and I. H. Pitman, J. Am. Chem. Soc. 97, 5566 (1975).Google Scholar
  312. 281.
    F. A. Sedor, D. G. Jacobson, and E. G. Sander, J. Am. Chem. Soc. 97, 5572 (1975).Google Scholar
  313. 282.
    D. E. Klinge and H. C. van der Pias, Rec. Trav. Chim. Pays-Bas 94, 233 (1975).Google Scholar
  314. 283.
    A. A. Morton, Solid Organoalkali Metal Reagents, Gordon and Breach Science Publishers, New York (1964), p. 123.Google Scholar
  315. 284.
    A. A. Morton, J. Org. Chem. 21, 593 (1956).Google Scholar
  316. 285.
    J. de Valk and H. C. van der Pias, Rec. Trav. Chim. Pays-Bas 90, 1239 (1971);Google Scholar
  317. H. C. van der Pias, Acc. Chem. Res. 11, 462 (1978).Google Scholar
  318. C. A. H. Rasmussen and H. C. van der Pias, Rec. Trav. Chim. Pays-Bas 96, 101 (1977);Google Scholar
  319. C. A. H. Rasmussen, H. C. van der Pias, P. Grotenhuis, and A. Koudijs, Heterocycl. Chem. 15, 1121 (1978);Google Scholar
  320. H. Rasmussen and H. C. van der Pias, Rec. Trav. Chim. Pays-Bas 98, 5 (1979).Google Scholar
  321. 287.
    H. C. van der Pias, P. Smit, and A. Koudijs, Tetrahedron Lett., 9 (1968).Google Scholar
  322. 288.
    (a) R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 276;Google Scholar
  323. (b).
    T. Kauffmann, R. Nürnberg, and R. Wirthwein, Chem. Ber. 102, 1161 (1969).Google Scholar
  324. 289.
    J. A. Zoltewicz and C. Nisi, J. Org. Chem. 34, 765 (1969).Google Scholar
  325. 290.
    G. Wittig and L. Pohmer, Angew. Chem. 67, 348 (1955).Google Scholar
  326. 291.
    G. Wittig and W. Herwig, Chem. Ber. 87, 1511 (1954).Google Scholar
  327. 292.
    G. Wittig and H. Härle, Justus Liebigs Ann. Chem. 623, 17 (1959).Google Scholar
  328. 293.
    N. Kharasch, T. G. Aiston, H. B. Lewis, and W. Wolf, Chem. Commun. 242 (1965).Google Scholar
  329. 294.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 109–111, 203.Google Scholar
  330. 295.
    T. L. Gilchrist, E. E. Nunn, and C. W. Rees, J. Chem. Soc. Perkin Trans. 1, 1262 (1974);Google Scholar
  331. J. W. Barton and D. J. Lapham, Tetrahedron Lett., 3571 (1979).Google Scholar
  332. 296.
    P. J. Garratt, Pure Appl. Chem. 44, 738 (1975).Google Scholar
  333. 297.
    P. J. Garratt and K. P. C. Vollhardt, J. Am. Chem. Soc. 94, 7087 (1972).Google Scholar
  334. 298.
    P. J. Garratt and S. B. Neoh, J. Org. Chem. 40, 970 (1975).Google Scholar
  335. 299.
    G. Wittig and R. Ludwig, Angew. Chem. 68, 40 (1956).Google Scholar
  336. 300.
    G. Wittig, Angew. Chem. 69, 245 (1957).Google Scholar
  337. 301.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), Chap. 3.Google Scholar
  338. 302.
    M. Jones, Jr. and R. H. Levin, J. Am. Chem. Soc. 91, 6411 (1969).Google Scholar
  339. 303.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 303.Google Scholar
  340. 304.
    A. Albert, Heterocyclic Chemistry, 2nd ed., Oxford University Press, New York (1968).Google Scholar
  341. 305.
    E. McNelis, J. Org. Chem. 30, 4324 (1965).Google Scholar
  342. 306.
    G. Wittig and E. Knauss, Chem. Ber. 91, 895 (1958).Google Scholar
  343. 307.
    J. Sauer, Angew. Chem. Int. Ed. Engl. 5, 211 (1966).Google Scholar
  344. 308.
    T. Zinke and H. Günther, Justus Liebigs Ann. Chem. 272, 243 (1893).Google Scholar
  345. 309.
    M. A. Ogliaruso, M. G. Romanelli, and E. I. Becker, Chem. Rev. 65, 261 (1965).Google Scholar
  346. 310.
    K. Rasheed, Tetrahedron 22, 2957 (1966).Google Scholar
  347. 311.
    G. Wittig, E. Knauss, and K. Niethammer, Justus Liebigs Ann. Chem. 630, 10 (1960).Google Scholar
  348. 312.
    G. Wittig and E. R. Wilson, Chem. Ber. 98, 451 (1965).Google Scholar
  349. 313.
    G. Wittig, J. Weinlich, and E. R. Wilson, Chem. Ber. 98, 458 (1965).Google Scholar
  350. 314.
    J. Sauer, A. Mielert, D. Lang, and D. Peter, Chem. Ber. 98, 1435 (1965).Google Scholar
  351. 315.
    J. Sauer, Angew. Chem. Int. Ed. Engl. 6, 16 (1967).Google Scholar
  352. 316.
    G. Seitz and T. Kämpchen, Chem. Ztg. 99, 292 (1975).Google Scholar
  353. 317.
    D. N. Reinhoudt and C. G. Kouwenhoven, Rec. Trav. Chim. Pays-Bas 93, 321 (1974).Google Scholar
  354. 318.
    G. Seitz and T. Kämpchen, Arch. Pharm. (Weinheim) 311, 728 (1978).Google Scholar
  355. 319.
    H. Gilman and R. D. Gorsich, J. Am. Chem. Soc. 79, 2625 (1957).Google Scholar
  356. 320.
    A. A. Morton, Solid Organoalkali Metal Reagents, Gordon and Breach Science Publishers, New York (1964), p. 122.Google Scholar
  357. 321.
    W. Tochterman, K. Oppenländer, and U. Walter, Chem. Ber. 97, 1318 (1964).Google Scholar
  358. 322.
    J. D. Cook and B. J. Wakefield, J. Chem. Soc. C, 1973 (1969).Google Scholar
  359. 323.
    D. L. Brydon, J. I. G. Cadogan, D. M. Smith, and J. B. Thomson, Chem. Commun., 727 (1967).Google Scholar
  360. 324.
    K. L. Shepard, Tetrahedron Lett., 3371 (1975);Google Scholar
  361. D. G. Gillespie, B. J. Walker, and D. Stevens, Tetrahedron Lett., 1905 (1976).Google Scholar
  362. 325.
    H. M. Walborsky and T. Bohnert, J. Org. Chem. 33, 3934 (1968).Google Scholar
  363. 326.
    L. W. Butz and A. W. Rytina, Org. React. 5, 136 (1949);Google Scholar
  364. S. L. Agarwal and S. K. Jain, Synthesis, 437 (1978).Google Scholar
  365. 327.
    G. Wittig and H. Heyn, Chem. Ber. 97, 1609 (1964).Google Scholar
  366. 328.
    G. Wittig and J. Heyn, Justus Liebigs Ann. Chem. 726, 57 (1969).Google Scholar
  367. 329.
    E. K. Fields and S. Meyerson, Acc. Chem. Res. 2, 273 (1969).Google Scholar
  368. 330.
    B. H. Klanderman, J. Am. Chem. Soc. 87, 4649 (1965).Google Scholar
  369. 331.
    A. Oku and A. Matsui, Bull. Chem. Soc. Japan 50, 3338 (1977).Google Scholar
  370. 332.
    M. S. Newman and R. Kannan, J. Org. Chem. 41, 3356 (1976).Google Scholar
  371. 333.
    P. Jayalekshmy and S. Mazur, J. Am. Chem. Soc. 98, 6710 (1976);Google Scholar
  372. S. Mazur and P. Jayalekshmy, J. Am. Chem. Soc. 101, 677 (1979).Google Scholar
  373. 334.
    J. Rebek, Jr., and F. Gavina, J. Am. Chem. Soc. 97, 3453 (1975);Google Scholar
  374. J. Rebek, Jr., Tetrahedron 35, 723 (1979).Google Scholar
  375. 335.
    N. D. Epiotis, W. R. Cherry, F. Bernardi, and W. J. Hehre, J. Am. Chem. Soc. 98, 4361 (1976).Google Scholar
  376. 336.
    R. Stoermer, Justus Liebigs Ann. Chem. 312, 237 (1900).Google Scholar
  377. 337.
    R. Stoermer, Justus Liebigs Ann. Chem. 313, 79 (1900).Google Scholar
  378. 338.
    H. Gilman and D. S. Meistrom, J. Am. Chem. Soc. 70, 1655 (1948).Google Scholar
  379. 339.
    H. Boos, unpublished results cited in G. Wittig, Pure Appl. Chem. 7, 173 (1963).Google Scholar
  380. 340.
    G. Wittig and H. Boos, unpublished results cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 305.Google Scholar
  381. 341.
    G. Wittig and H. Boos, unpublished results cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  382. 342.
    H. Gilman and R. D. Gorsich, J. Am. Chem. Soc. 78, 2217 (1956).Google Scholar
  383. 343.
    M. Cugon de Sevricourt and M. Robba, Bull. Soc. Chim. Fr., 142 (1977).Google Scholar
  384. 344.
    G. Wittig and G. Kolb, unpublished results cited in G. Wittig, Angew. Chem. Int. Ed. Engl. 1, 415 (1962).Google Scholar
  385. 345.
    G. Wittig and G. Kolb, unpublished results cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 291.Google Scholar
  386. 346.
    G. Kolb, dissertation, University of Heidelberg (1959), cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  387. 347.
    G. Wittig, Angew. Chem. Int. Ed. 1, 415 (1962).Google Scholar
  388. 348.
    G. Wittig and H. Boos, unpublished results cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 291.Google Scholar
  389. 349.
    H. Gilman and G. F. Wright, J. Am. Chem. Soc. 55, 3302 (1933).Google Scholar
  390. 350.
    L. D. Tarasova and Y. L. Gol’dfarb, Bull. Acad. Sei. USSR Div. Chem. Sci., 1978 (1965).Google Scholar
  391. 351.
    R. Somay, J. Meunier, and P. Fournari, Bull. Soc. Chim. Fr., 990 (1971).Google Scholar
  392. G. M. Davies and P. S. Davies, Tetrahedron Lett., 3507 (1972).Google Scholar
  393. 353.
    M. Blumenthal, Chem. Ber. 7, 1092 (1874).Google Scholar
  394. 354.
    K. Dziewonski, Chem. Ber. 36, 962 (1903).Google Scholar
  395. 355.
    J. I. Jones, Chem. Commun., 938 (1967).Google Scholar
  396. 356.
    M. E. Synerholm, J. Am. Chem. Soc. 67, 1229 (1945).Google Scholar
  397. 357.
    H.-D. Scharf, H. Leismann, and H. Lechner, Chem. Ber. 104, 847 (1971).Google Scholar
  398. 358.
    T. Matsuo and S. Mihara, Bull. Chem. Soc. Japan 48, 3660 (1975).Google Scholar
  399. 359.
    A. Michael and J. E. Bucher, Chem. Ber. 28, 2511 (1895);Google Scholar
  400. R. N. Misra and S. Dutt, J. Ind. Chem. Soc. 13, 98 (1936);Google Scholar
  401. R. N. Misra and S. Dutt, J. Ind. Chem. Soc. 13, 98 (1936).Google Scholar
  402. 360.
    L. Crombie, P. A. Gilbert, and R. P. Houghton, J. Chem. Soc. C, 130 (1968).Google Scholar
  403. 361.
    J. L. Ripoll, P. Blickle, and H. Hopf, unpublished results cited in G. Weber, K. Menke, and H. Hopf, Chem. Ber. 113, 531 (1980).Google Scholar
  404. 362.
    A. Szabo, dissertation, University of Tübingen (1975).Google Scholar
  405. 363.
    (a) J. LeFevre and J. Hamelin, Tetrahedron Lett., 1757 (1979);Google Scholar
  406. (b) G. Rosskamp and H. Suhr, Justus Liebigs Ann. Chem. 1478 (1975).Google Scholar
  407. 364.
    H. Müller, dissertation, University of Heidelberg (1964) cited in G. Wittig, Pure Appl. Chem. 7, 173 (1963).Google Scholar
  408. 365.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 291.Google Scholar
  409. 366.
    H. Müller, dissertation, University of Heidelberg (1964), cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  410. 367.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 289.Google Scholar
  411. 368.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 305.Google Scholar
  412. 369.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 299.Google Scholar
  413. 370.
    H. Müller, dissertation, University of Heidelberg (1964), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 295.Google Scholar
  414. R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), (a) p. 295; (b) pp. 135–145.Google Scholar
  415. 372.
    D. A. Shirley and P. A. Roussel, J. Am. Chem. Soc. 75, 375 (1953).Google Scholar
  416. 373.
    J. Bergman and N. Eklund, Tetrahedron 36, 1439 (1980);Google Scholar
  417. J. Bergman and N. Eklund, Tetrahedron 36, 1445 (1980).Google Scholar
  418. 374.
    H. Müller, dissertation, University of Heidelberg (1964), cited in J. Bergman and N. Eklund, Tetrahedron 36, 1439 (1980).Google Scholar
  419. 375.
    M. P. Cava and L. Bravo, Tetrahedron Lett., 4631 (1970).Google Scholar
  420. 376.
    R. F. C. Brown, W. D. Crow, and R. K. Solly, Chem. Ind. (London), 343 (1966);Google Scholar
  421. M. P. Cava and L. Bravo, Chem. Commun., 1538 (1968).Google Scholar
  422. 377.
    M. M. King, Ann. Rep. Petr. Res. Found. 18, 117 (1973).Google Scholar
  423. 378.
    R. H. Brown, dissertation, New York University (1975); Diss. Abstr. 36, 5586B (1976).Google Scholar
  424. 379.
    D. Kumfer, Anal Biochem. 8, 75 (1964).Google Scholar
  425. 380.
    R. A. J. Clark and J. Parrick, Org. Mass Spectrom. 12, 421 (1977).Google Scholar
  426. 381.
    P. Mencarelli and F. Stegel, J. Chem. Soc. Chem. Commun., 564 (1978);Google Scholar
  427. L. Bonaccina, P. Mencarelli, and F. Stegel, J. Org. Chem. 44, 4420 (1979);Google Scholar
  428. P. Mencarelli and F. Stegel, J. Chem. Soc. Chem. Commun., 123 (1980).Google Scholar
  429. 382.
    W. Draber, Chem. Ber. 100, 1559 (1967).Google Scholar
  430. 383.
    J. F. Liebman and A. Greenberg, Chem. Rev. 76, 311 (1976).Google Scholar
  431. 383a.
    K. M. Wald, A. A. Nada, G. Szilagyi, and H. Wamhoff, Chem. Ber. 113, 2884 (1980).Google Scholar
  432. 384.
    V. Wahl, dissertation, University of Heidelberg (1962), cited in R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 292.Google Scholar
  433. 385.
    M. D. Rausch, T. R. Criswell, and A. K. Ignatowicz, J. Organometal Chem. 13, 419 (1968).Google Scholar
  434. 386.
    V. Wahl, dissertation, University of Heidelberg (1962), cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  435. 387.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 196.Google Scholar
  436. 388.
    H. Wynberg, H. van Driel, R. M. Kellog, and J. Buter, J. Am. Chem. Soc. 89, 3487 (1967).Google Scholar
  437. 389.
    M. Rings, dissertation, University of Heidelberg (1966), cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968).Google Scholar
  438. 390.
    L. Friedman and D. F. Lindow, J. Am. Chem. Soc. 90, 2329 (1968).Google Scholar
  439. 391.
    I. Tabushi, H. Yamada, Z. Yoshida, and R. Oda, Bull Chem. Soc. Japan 50, 285 (1977).Google Scholar
  440. 392.
    S.-O. Lawesson, Ark. Kemi 11, 373 (1957).Google Scholar
  441. 393.
    W. Steinkopf, Justus Liebigs Ann. Chem. 543, 128 (1940).Google Scholar
  442. 394.
    S. Gronowitz, P. Moses, and R. Hakansson, Ark. Kemi 16, 267 (1960).Google Scholar
  443. 395.
    P. Moses and S. Gronowitz, Ark. Kemi 18, 119 (1961).Google Scholar
  444. 396.
    B. Ostman, Ark. Kemi 22, 551 (1964).Google Scholar
  445. 397.
    S. Gronowitz and U. Rosen, Chem. Scr. 1, 33 (1971).Google Scholar
  446. 398.
    S. Gronowitz and U. Rosen, unpublished results cited in S. Gronowitz and B. Holm, Acta Chem. Scand. 23, 2207 (1969).Google Scholar
  447. 399.
    S. Gronowitz and B. Holm, Acta Chem. Scand. 23, 2207 (1969).Google Scholar
  448. 400.
    S. Gronowitz and B. Holm, Acta Chem. Scand. Ser. B 30, 505 (1976).Google Scholar
  449. 401.
    H. Christiansen, S. Gronowitz, B. Rodmar, S. Rodmar, U. Rosen, and M. K. Sharma, Ark. Kemi 30, 561 (1968).Google Scholar
  450. 402.
    B. E. Ayers, S. W. Longworth, and J. F. W. McOmie, Tetrahedron 31, 1755 (1975).Google Scholar
  451. 403.
    M. C. Ford and D. Mackay, J. Chem. Soc., 4985 (1956).Google Scholar
  452. 404.
    A.-B. Hornfeldt and P.-O. Sundberg, Acta Chem. Scand. 26, 31 (1972).Google Scholar
  453. 405.
    L. Schmerling, J. Am. Chem. Soc. 67, 1438 (1945).Google Scholar
  454. 406.
    H. W. Adickes, dissertation, Texas Christian University (1968).Google Scholar
  455. 407.
    L. van der Does and H. J. den Hertog, Rec. Trav. Chim. Pays-Bas 91, 1403 (1972).Google Scholar
  456. 408.
    J. F. Bunnett and B. F. Gloor, Heterocycles 5, 377 (1976).Google Scholar
  457. 409.
    C. Dell’Erba, D. Spinelli, and G. Leandri, Gazz. Chim. Ital. 99, 535 (1969).Google Scholar
  458. 410.
    M. Novi, G. Guanti, C. Dell’Erba, and D. Spinelli, J. Chem. Soc. Perkin Trans. 1, 2264 (1976).Google Scholar
  459. 411.
    M. Novi, G. Guanti, F. Sancassan, and C. Dell’Erba, J. Chem. Soc. Perkin Trans. 1, 1140 (1978).Google Scholar
  460. 412.
    R. H. Walter, dissertation, Texas Christian University (1974).Google Scholar
  461. Farbwerke Hoechst Aktiengesellschaft, Brit. Pat., 837,086 (1960); Chem. Abstr. 54, 24798e (1960).Google Scholar
  462. 414.
    M. G. Reinecke and H. H. Ballard, Abstracts of the 159th National Meeting of the American Chemical Society, Houston, TX, American Chemical Society, ORGN 12 (1970).Google Scholar
  463. 415.
    M. G. Reinecke and R. H. Walter, J. Chem. Soc. Chem. Commun., 1044 (1974).Google Scholar
  464. 416.
    H. Zollinger, Azo and Diazo Chemistry, Interscience, New York (1961), p. 239.Google Scholar
  465. 417.
    R. Promel, A. Cardon, M. Daniel, G. Jacques, and A. Vandersmissen, Tetrahedron Lett., 3067 (1968).Google Scholar
  466. 418.
    M. Tiecco and A. Tundo, Int. J. Sulfur Chem. 8, 295 (1973).Google Scholar
  467. 419.
    G. Vernin, Bull. Soc. Chim. Fr., 1257 (1976).Google Scholar
  468. 420.
    G. Martelli, P. Spagnolo, and M. Tiecco, J. Chem. Soc. B, 901 (1968).Google Scholar
  469. 421.
    D. Mackay, Can. J. Chem. 44, 2881 (1966).Google Scholar
  470. 422.
    K. Undheim, O. Thorstad, and G. Hvistendahl, Org. Mass Spectrom. 5, 73 (1971).Google Scholar
  471. 423.
    M. Bartle, S. T. Gore, R. K. Mackie, and J. M. Tedder, J. Chem. Soc. Perkin Trans. 1, 1636 (1976);Google Scholar
  472. S. T. Gore, R. K. Mackie, and J. M. Tedder, J. Chem. Soc. Perkin Trans. 1, 1639 (1976).Google Scholar
  473. 424.
    The photolysis of 2,3-diiodothiophene (360) and 2,3-diiodothianaphthene (466, Br=I) has also been studied with a view toward generating the arynes 4 and 26, respectively, but no results have ever been reported, apparently; H. Wynberg, H. van Driel, R. M. Kellogg, and J. Buter, J. Am. Chem. Soc. 89, 3487 (1967).Google Scholar
  474. 425.
    E. K. Fields and S. Meyerson, J. Org. Chem. 35, 67 (1970).Google Scholar
  475. 426.
    E. K. Fields and S. Meyerson, Abstracts of the Fourth International Congress of Heterocyclic Chemistry, Salt Lake City, 1973, p. 284.Google Scholar
  476. 427.
    H. Wynberg and A. Bantjes, J. Org. Chem. 24, 1421 (1959).Google Scholar
  477. 428.
    C. D. Hurd, R. V. Levetan, and A. R. Macon, J. Am. Chem. Soc. 84, 4515 (1962).Google Scholar
  478. 428a.
    D. Del Mazza and M. G. Reinecke, J. Chem. Soc. Chem. Commun. 124 (1981).Google Scholar
  479. 428b.
    M. R. Bryce and J. M. Vernon, Adv. Heterocycl. Chem. 28, 183 (1981).Google Scholar
  480. 429.
    D. Del Mazza and M. G. Reinecke, Heterocycles 14, 647 (1980).Google Scholar
  481. 430.
    D. D. Callander, P. L. Coe, J. C. Tatlow, and A. J. Uff, Tetrahedron 25, 25 (1969).Google Scholar
  482. 431.
    S. Meyerson and E. K. Fields, J. Org. Chem. 33, 847 (1968).Google Scholar
  483. 432.
    H. Wynberg, J. deWit, and H. J. M. Sinnige, J. Org. Chem. 35, 711 (1970).Google Scholar
  484. 433.
    J. G. Newsom, dissertation, Texas Christian University (1977).Google Scholar
  485. 434.
    K. Tserng and L. Bauer, J. Org. Chem. 40, 172 (1975).Google Scholar
  486. 435.
    D. W. H. MacDowell and F. L. Bailas, J. Org. Chem. 42, 3717 (1977);Google Scholar
  487. D. Binder and P. Stanetty, Synthesis, 200 (1977).Google Scholar
  488. 436.
    M. G. Reinecke, J. G. Newsom, and K. A. Almqvist, Synthesis, 327 (1980).Google Scholar
  489. 437.
    G. Schaden, Justus Liebigs Ann. Chem. 559 (1978).Google Scholar
  490. 438.
    H.-F. Grützmacher and U. Straetmaus, Tetrahedron 36, 807 (1980).Google Scholar
  491. 439.
    H. Wynberg and A. J. H. Klunder, Rec. Trav. Chim. Pays-Bas 88, 328 (1969)Google Scholar
  492. J. deWit and H. Wynberg, Tetrahedron 29, 1379 (1973).Google Scholar
  493. 440.
    W. J. Feast, W. K. R. Musgrave, and W. E. Preston, J. Chem. Soc. Perkin Trans. 1 1830 (1972).Google Scholar
  494. 441.
    E. A. Braude, R. P. Linstead, and P. W. D. Mitchell, J. Chem. Soc., 3578 (1954).Google Scholar
  495. 442.
    R. Weiss, Org. Synth. Coll. Vol. 3, 729 (1955).Google Scholar
  496. 443.
    E. A. Braude, L. M. Jackman, and R. P. Linstead, J. Chem. Soc., 3548 (1954).Google Scholar
  497. 444.
    H. von Brachel and U. Bahr, in Houben-Weyl, Methoden der Organischen Chemie, Vol. 5, E. Muller, Ed., George Theime Verlag, Stuttgart (1970), Part lc, p. 967.Google Scholar
  498. 445.
    T. J. Barton, M. D. Martz, and R. G. Zika, J. Org. Chem. 37, 552 (1972).Google Scholar
  499. 446.
    D. N. Reinhoudt, Adv. Heterocycl Chem. 21, 253 (1977).Google Scholar
  500. 447.
    M. C. Kloetzel, Org. React. 4, 1 (1948).Google Scholar
  501. 448.
    T. Eicher and J. L. Weber, Top. Curr. Chem. 57, 1 (1975).Google Scholar
  502. 449.
    K. T. Potts and J. S. Baum, Chem. Rev. 74, 189 (1974).Google Scholar
  503. 450.
    B. Haiton, Chem. Rev. 73, 113 (1973).Google Scholar
  504. 451.
    H. H. Wasserman, G. M. Clark, and P. C. Turley, Top. Curr. Chem. 47, 73 (1971).Google Scholar
  505. 452.
    A. Amano, T. Mukai, T. Nakazawa, and K. Okoyama, Bull Chem. Soc. Japan 49, 1671 (1976).Google Scholar
  506. 453.
    M. G. Reinecke, L.-J. Chen, and A. Almqvist, J. Chem. Soc. Chem. Commun. 585 (1980).Google Scholar
  507. 454.
    R. Wheland and P. D. Bartlett, J. Am. Chem. Soc. 92, 6057 (1970);Google Scholar
  508. A. Padwa and P. H. J. Carisen, J. Am. Chem. Soc. 99, 1514 (1977);Google Scholar
  509. N. Shimizu and P. D. Bartlett, J. Am. Chem. Soc. 100, 4260 (1978).Google Scholar
  510. 455.
    B. M. Trost and P. J. Whitman, J. Am. Chem. Soc. 96, 7421 (1974).Google Scholar
  511. 456.
    T. Yonezawa, H. Konishi, and H. Kato, Bull Chem. Soc. Japan 42, 933 (1969).Google Scholar
  512. 457.
    A. N. Korepanov, T. A. Danilova, and E. Z. Viktorova, Chem. Heterocycl Comp. (USSR), 868 (1977); (b) M. G. Reinecke, J. G. Newson, and K. A. Almqvist, Tetrahedron 37, in press (1981).Google Scholar
  513. 458.
    G. Wittig and H. Dürr, Justus Liebigs Ann. Chem. 672, 55 (1964).Google Scholar
  514. 459.
    J. A. Berson, P. B. Dervan, R. Malherbe, and J. A. Jenkins, J. Am. Chem. Soc. 98, 5937 (1976).Google Scholar
  515. 460.
    P. Crews and J. Beard, J. Org. Chem. 38, 522 (1973).Google Scholar
  516. 461.
    H. M. R. Hoffmann, Angew. Chem. Int. Ed. Engl 8, 556 (1969).Google Scholar
  517. 462.
    R. W. Hoffman, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 197.Google Scholar
  518. 463.
    J. H. Wotiz, in Chemistry of Acetylenes, H. G. Viehe, Ed., Marcel Dekker, New York (1969), Chap. 7, p. 365.Google Scholar
  519. 464.
    T. Sakai and M. Hattori, Chem. Lett., 617 (1974).Google Scholar
  520. 465.
    H. Suhr, Angew. Chem. Int. Ed. Engl. 11, 781 (1972).Google Scholar
  521. 466.
    H. Suhr and G. Kruppa, Justus Liebigs Ann. Chem. 744, 1 (1971).Google Scholar
  522. 467.
    P. E. Fjelstad and K. Undheim, Acta Chem. Scand. Ser. B 30, 375 (1976).Google Scholar
  523. 468.
    H. Suhr, unpublished results cited in A. Szabo, dissertation, University of Tübingen (1975).Google Scholar
  524. 469.
    E. Sinkinson, Ind. Eng. Chem. 17, 27 (1925).Google Scholar
  525. 470.
    R. Srinivasin, J. Am. Chem. Soc. 89, 1758 (1967).Google Scholar
  526. 471.
    H. H. Wasserman and L. S. Keller, Chem. Commun., 1483 (1970).Google Scholar
  527. 472.
    M. L. Deem, Synthesis, 675 (1972).Google Scholar
  528. 473.
    J. A. Berson and M. Pomerantz, J. Am. Chem. Soc. 86, 3896 (1964).Google Scholar
  529. 474.
    H. Suhr and A. Szabo, Justus Liebigs Ann. Chem., 342 (1975).Google Scholar
  530. 475.
    G. Martelli, P. Spagnolo, and M. Tiecco, Chem. Commun., 282 (1969).Google Scholar
  531. 476.
    C. F. Cullis, D. J. Hucknall, and J. V. Shepherd, Proc. R. Soc. Ser. A 335, 525 (1973).ADSGoogle Scholar
  532. 477.
    S. Gronowitz and T. Frejd, Acta Chem. Scand. Ser. B 30, 485 (1976).Google Scholar
  533. 478.
    M. Rings, dissertation, University of Heidelberg (1966);Google Scholar
  534. (b).
    F. M. Stoyanovich, Y. L. Gol’dfarb, and G. B. Chermanova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 2228 (1973);Google Scholar
  535. (c).
    F. M. Stoyanovich, M. A. Marakatkina, and Y. L. Gol’dfarb, Bull. Acad. Sci. USSR, Div. Chem. Sci., 2362 (1976).Google Scholar
  536. 479.
    Y. Matsuki and Y. Adachi, Nippon Kagaku Zasshi 89, 192 (1968).Google Scholar
  537. 480.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 288–289.Google Scholar
  538. 481.
    M. G. Reinecke, W. B. Mohr, H. W. Adickes, D. A. deBie, H. C. van der Plas, and K. Nijdam, J. Org. Chem. 38, 1365 (1973).Google Scholar
  539. 482.
    G. Komppa, J. Prakt. Chem. 122, 319 (1929).Google Scholar
  540. 483.
    R. P. Dickinson and B. Iddon, J. Chem. Soc. C, 2733 (1968).Google Scholar
  541. 484.
    K. E. Chippendale, B. Iddon, H. Suschitzky, and D. S. Taylor, J. Chem. Soc. Perkin Trans. 1, 1168 (1974).Google Scholar
  542. 485.
    P. Grandclaudon and A. Lablache-Combier, J. Org. Chem. 43, 4379 (1978).Google Scholar
  543. 486.
    W. Ried and H. Bender, Chem. Ber. 88, 34 (1955).Google Scholar
  544. 487.
    R. D. Schuetz, D. D. Taft, J. P. O’Brien, J. L. Shea, and H. H. Mork, J. Org. Chem. 28, 1420 (1963).Google Scholar
  545. 488.
    R. P. Dickinson and B. Iddon, J. Chem. Soc. C, 3447 (1971).Google Scholar
  546. 489.
    M. J. Cook, A. R. Katritzky, and P. Linda, Adv. Heterocycl. Chem. 17, 255 (1974).Google Scholar
  547. 490.
    H. D. Hartough and S. L. Meisel, Compounds with Condensed Thiophene Rings, A. Weissberger, Ed., Wiley-Interscience, New York (1954), p. 159.Google Scholar
  548. 491.
    B. Iddon and R. M. Scrowston, Adv. Heterocycl. Chem. 11, 177 (1970).Google Scholar
  549. 492.
    F. G. Bordwell and C. J. Albisetti, Jr., J. Am. Chem. Soc. 70, 1558 (1948).Google Scholar
  550. 493.
    F. Sauter and U. Jordis, Monatsh. Chem. 105, 1252 (1974).Google Scholar
  551. 494.
    A. H. Schlesinger and D. T. Mowry, J. Am. Chem. Soc. 73, 2614 (1951).Google Scholar
  552. Although the structure of this product has been questioned (footnote 29 in Reference 1) its nmr spectrum496 is quite consistent with the assignment: ó = 7.7, m(4); 5.2, d, J= 1 Hz (1); 4.7, d,J=lHz (1); 2.7, m(4); 1.6, m(6).Google Scholar
  553. 496.
    H. W. Adickes, unpublished results (1968).Google Scholar
  554. 497.
    T. A. Hollingworth, Jr., M. S. thesis, Texas Christian University (1967).Google Scholar
  555. 498.
    S. Gronowitz and T. Frejd, Acta Chem. Scand. Ser. B 30, 439 (1976).Google Scholar
  556. 499.
    T. Frejd, Chem. Scr. 10, 133 (1976).Google Scholar
  557. 500.
    T. Quang Minh, L. Christiaens, and M. Renson, Bull. Soc. Chim. Fr., 2239 (1974).Google Scholar
  558. 501.
    A. I. Shatenshtein, A. G. Kamrad, I. O. Shapiro, Y. I. Ranneva, and E. N. Zvyagintseva, Dokl. Chem. 168, 502 (1966).Google Scholar
  559. 502.
    T. L. Gilchrist and D. P. J. Pearson, J. Chem. Soc. Perkin Trans. 1, 989 (1976);Google Scholar
  560. S. Gronowitz and T. Frejd, Chem. Heterocycl. Comp. 14, 353 (1978).Google Scholar
  561. 503.
    T. Quang Minh, L. Christiaens, and M. Renson, Bull. Soc. Chim. Fr., 2244 (1974).Google Scholar
  562. 504.
    H. Boer and H. J. den Hertog, Tetrahedron Lett., 1943 (1969).Google Scholar
  563. 505.
    H. N. M. van der Lans, H. J. den Hertog, and A. van Veldhuizen, Tetrahedron Lett., 1875 (1971);Google Scholar
  564. G. E. Lewis, R. H. Prager, and R. H. M. Ross, Aust. J. Chem. 28, 2057 (1975).Google Scholar
  565. 506.
    G. M. Sanders, M. van Dijk, and H. J. den Hertog, Rec. Trav. Chim. Pays-Bas 93, 273 (1974).Google Scholar
  566. 507.
    H. W. van Meeteren and H. C. van der Plas, Rec. Trav. Chim. Pays-Bas 90, 105 (1971).Google Scholar
  567. 508.
    T. Kauffmann, H. Fischer, R. Nürnberg, M. Vestweber, and R. Wirthwein, Tetrahedron Lett., 2917 (1967).Google Scholar
  568. 509.
    M. R. Grimmett, Adv. Heterocycl. Chem. 12, 103 (1970).Google Scholar
  569. 510.
    B. A. Tertov and A. S. Morkovnik, J. Org. Chem. USSR 9, 2222 (1974).Google Scholar
  570. 511.
    G. M. Sanders, M. van Dijk, and H. J. den Hertog, Tetrahedron Lett., 4717 (1972).Google Scholar
  571. 512.
    E. S. Hand and W. W. Paudler, J. Org. Chem. 43, 2900 (1978).Google Scholar
  572. 513.
    E. S. Hand and W. W. Paudler, J. Org. Chem. 41, 3549 (1976).Google Scholar
  573. 513.
    R. Ketcham and E. Schaumann, J. Org. Chem. 45, 3748 (1980);Google Scholar
  574. (b).
    N. Jacobsen, P. de Mayo, and A. C. Weedon, Nouv. J. Chim. 2, 331 (1978);Google Scholar
  575. (c).
    J. P. Snyder, in Organic Sulphur Chemistry, C. J. M. Stirling, Ed., Butterworths, London (1974), p. 307;Google Scholar
  576. H. E. Simmons, R. D. Vest, D. C. Blomstrom, J. R. Roland, and T. L. Cairns, J. Am. Chem. Soc. 84, 4746 (1962).Google Scholar
  577. 514.
    (a) C. W. Rees and R. C. Storr, J. Chem. Soc. C, 765 (1969);Google Scholar
  578. (b).
    P. Blatcher, D. Mid- dlemiss, P. Murray-Rust, and J. Murray-Rust, Tetrahedron Lett., 4193 (1980);Google Scholar
  579. (c).
    A. Galbraith, T. Small, R. A. Barnes, and V. Boekelheide, J. Am. Chem. Soc. 83, 453 (1961).Google Scholar
  580. 515.
    R. Fusco, V. Rosnati, and G. Pagani, Tetrahedron Lett., 1739 (1966).Google Scholar
  581. 516.
    M. Begtrup, Acta Chem. Scand. 24, 1819 (1970)Google Scholar
  582. M. Begtrup, Acta Chem. Scand. 27, 2051 (1973).Google Scholar
  583. 517.
    (a) B. Stanovnik, M. Tišler, J. Bradač, B. Budič, B. Koren, and B. Mozetič-Reščič, Heterocycles 12, 457 (1979);Google Scholar
  584. (b).
    M. Bosco, L. Forlani, P. E. Todesco, and L. Troisi, J. Chem. Soc. D, 1093 (1971);Google Scholar
  585. L. Forlani, P. E. Todesco, and L. Troisi, J. Chem. Soc. Perkin Trans. 2, 1016 (1978).Google Scholar
  586. 518.
    M. Bosco, L. Forlani, P. E. Todesco, and L. Troisi, J. Chem. Soc. Perkin Trans. 1, 398 (1976).Google Scholar
  587. 519.
    Y. Tamura, T. Miyamoto, and M. Ikeda, Chem. Ind. (London), 1439 (1971).Google Scholar
  588. 520.
    R. Motoyama, K. Sato, and E. Imoto, Nippon Kagaku Zasshi 78, 779 (1957); Chem. Abstr. 54, 22559f (1960).Google Scholar
  589. 521.
    May and Baker Ltd., Belg. Pat. 629,580; Chem. Abstr. 60, 15875f (1964).Google Scholar
  590. 522.
    T. Naito, S. Nakagawa, and K. Takahashi, Chem. Pharm. Bull. (Tokyo) 16, 148 (1968).Google Scholar
  591. 523.
    J. K. Kim and J. F. Bunnett, J. Am. Chem. Soc. 92, 7463 (1970).Google Scholar
  592. 524.
    R. E. Smith, dissertation, University of North Carolina (1966).Google Scholar
  593. 525.
    R. L. McKee, University of North Carolina, personal communication (1977).Google Scholar
  594. 526.
    L. M. Weinstock and P. I. Pollok, Adv. Heterocycl. Chem. 9, 107 (1968).Google Scholar
  595. 527.
    C. W. Bird and C. K. Wong, Tetrahedron Lett., 2143 (1971).Google Scholar
  596. 528.
    S. Uemura, A. Toshimitsu, and M. Okano, J. Chem. Soc. Perkin Trans. 1, 1076 (1978).Google Scholar
  597. 529.
    H. Gilman, H. B. Willis, and J. Swislowsky, J. Am. Chem. Soc. 61, 1371 (1939).Google Scholar
  598. 530.
    M. Julia, Y. Huang, and J. Igolen, C. R. Acad. Sci. Ser. C 265, 110 (1967).Google Scholar
  599. 531.
    J. Igolen and A. Kolb, C. R. Acad. Sci. Ser. C 269, 54 (1969).Google Scholar
  600. 532.
    M. Julia, J. Igolen, and A. Kolb, C. R. Acad. Sci. Ser. C 273, 1776 (1971).Google Scholar
  601. 533.
    D. J. Cram and A. C. Day, J. Org. Chem. 31, 1227 (1966).Google Scholar
  602. 534.
    M. Julia, F. LeGoffic, J. Igolen, and M. Baillarge, C. R. Acad. Sci. Ser. C 264, 118 (1967);Google Scholar
  603. M. Julia, F. LeGoffic, J. Igolen, and M. Baillarge, Bull. Soc. Chim. Fr., 1071 (1968).Google Scholar
  604. M. Julia, F. LeGoffic, J. Igolen, and M. Baillarge, Tetrahedron Lett., 1569 (1969).Google Scholar
  605. R. C. Perera and R. K. Smalley, J. Chem. Soc. D, 1458 (1970).Google Scholar
  606. L. DiNunno, S. Florio, and P. E. Todesco, Tetrahedron 30, 863 (1974).Google Scholar
  607. L. DiNunno, S. Florio, and P. E. Todesco, Tetrahedron 32, 1037 (1976);Google Scholar
  608. L. DiNunno and S. Florio, Tetrahedron 33, 1523 (1977).Google Scholar
  609. L. DiNunno, S. Florio, and P. E. Todesco, J. Chem. Soc. Perkin Trans. 2 1171 (1974).Google Scholar
  610. Y. Matsuki and F. Shoji, Nippon Kagaku Zasshi 86, 1067 (1965); Chem. Abstr. 65, 13638g (1966);Google Scholar
  611. Y. Matsuki and I. Ito, Nippon Kagaku Zasshi 88, 758 (1967); Chem. Abstr. 69, 59018 (1968).Google Scholar
  612. F. Ciminale, G. Bruno, L. Testaferri, M. Tiecco, and G. Martelli, J. Org. Chem. 43, 4509 (1978)Google Scholar
  613. 542.
    R. P. Dickinson and B. Iddon, J. Chem. Soc. C, 182 (1971).Google Scholar
  614. 543.
    E. Waldvogel, G. Schwarb, J. M. Bastian, and J. P. Bourquin, Helv. Chim. Acta 59, 866 (1976).Google Scholar
  615. 544.
    O. L. Chapman, R. S. Sheridan, and J.-P. LeRoux, Rec. Trav. Chim. Pays-Bas 98, 334 (1979)Google Scholar
  616. (b).
    J. Rigaudy, C. Igier, and J. Barcelo, Tetrahedron Lett., 1837 (1979);Google Scholar
  617. R. Dunkin and P. C. P. Thomson, J. Chem. Soc., Chem. Commun., 499 (1980);Google Scholar
  618. (c).
    P. T. Gallagher, B. Iddon, and H. Suschitzky, J. Chem. Soc. Perkin Trans. 1, 2362 (1980).Google Scholar
  619. 545.
    J. W. Huffman, L. H. Keith, and R. L. Asbury, J. Org. Chem. 30, 1600 (1965).Google Scholar
  620. 546.
    F. L. Hedberg and H. Rosenberg, Tetrahedron Lett., 4011 (1969).Google Scholar
  621. 547.
    J. F. Eastham and G. W. Gibson, J. Am. Chem. Soc. 585, 2171 (1963).Google Scholar
  622. 548.
    M. Walczak, K. Walczak, R. Mink, M. D. Rausch, and G. Stucky, J. Am. Chem. Soc. 100, 6382 (1978).Google Scholar
  623. 549.
    D. W. Slocum, R. L. Marchai, and W. E. Jones, J. Chem. Soc. Chem. Commun., 967 (1974).Google Scholar
  624. 550.
    J. W. Huffman and J. F. Cope, J. Org. Chem. 36, 4068 (1971).Google Scholar
  625. 551.
    A. N. Nesmeyanov, B. A. Sazonova, and N. S. Sazonova, Dokl. Chem. 176, 843 (1967).Google Scholar
  626. 552.
    E. W. Neuse and L. Bednarik, Macromolecules 12, 187 (1979).ADSGoogle Scholar
  627. 553.
    J. C. Martin and D. R. Bloch, J. Am. Chem. Soc. 93, 451 (1971).Google Scholar
  628. 554.
    T. Kauffmann and H. Marhan, Chem. Ber. 96, 2519 (1963).Google Scholar
  629. 555.
    R. A. Abramovitch and G. M. Singer, J. Org. Chem. 39, 1795 (1974).Google Scholar
  630. 556.
    Y. Apeloig, P. v. R. Schleyer, and J. A. Pople, J. Am. Chem. Soc. 99, 1291 (1977).Google Scholar
  631. 557.
    C. L. Habraken and E. K. Poels, J. Org. Chem. 42, 2893 (1977);Google Scholar
  632. P. Cohen-Fernandes, C. Erkelens, C. G. M. van Eendenburg, J. J. Verhoeven, and C. L. Habraken, J. Org. Chem. 44, 4156 (1979).Google Scholar
  633. 558.
    C. G. Swain, J. E. Sheats, and K. G. Harbison, J. Am. Chem. Soc. 97, 783 (1975);Google Scholar
  634. L. R. Subramanian, M. Hanack, L. W. K. Chang, M. A. Imhoff, P. v. R. Schleyer, F. Effenberger, W. Kurtz, P. J. Stang, and T. E. Dueber, J. Org. Chem. 41, 4099 (1976).Google Scholar
  635. 559.
    R. N. Butler, Chem. Rev. 75, 241 (1975).ADSGoogle Scholar
  636. 560.
    J. M. Tedder, Adv. Heterocycl. Chem. 8, 1 (1967).ADSGoogle Scholar
  637. 561.
    M. Tišler and B. Stanovnik, Heterocycles 4, 1115 (1976).Google Scholar
  638. 562.
    R. O. Duthaler, H. G. Forster, and J. D. Roberts, J. Am. Chem. Soc. 100, 4974 (1978).Google Scholar
  639. 563.
    G. F. Koser, J. Org. Chem. 42, 1474 (1977)Google Scholar
  640. R. A. Abramovitch and J. G. Saha, Can. J. Chem. 43, 3269 (1965);Google Scholar
  641. R. W. Taft, J. Am. Chem. Soc. 83, 3350 (1961).Google Scholar
  642. 564.
    W. A. Sheppard and O. W. Webster, J. Am. Chem. Soc. 95, 2695 (1973).Google Scholar
  643. 565.
    P. Gronski and K. Hartke, Chem. Ber. 111, 272 (1978).Google Scholar
  644. 566.
    M. Kocevar, B. Stanovnik, and M. Tisler, Heterocycles 6, 681 (1977).Google Scholar
  645. W. A. Sheppard, G. W. Gokel, O. W. Webster, K. Betterton, and J. W. Timberake, J. Org. Chem. 44, 1717 (1979).Google Scholar
  646. 566b.
    M. Kocevar, B. Stanovnik, and M. Tisler, Heterocycles 6, 681 (1977).Google Scholar
  647. 567.
    W. L. Magee and H. Shechter, J. Am. Chem. Soc. 99, 633 (1977).Google Scholar
  648. 568.
    H. Durr and H. Schmitz, Chem. Ber. 111, 2258 (1978).Google Scholar
  649. 569.
    P. B. Shevlin, J. Am. Chem. Soc. 94, 1379 (1972);Google Scholar
  650. Reactive Intermediates, R. A. Abramovitch, Ed., Vol. I, Plenum Press, New York (1980), Chap. 1.Google Scholar
  651. 570.
    K. L. Kirk and L. Cohen, J. Am. Chem. Soc. 95, 4619 (1973).Google Scholar
  652. 571.
    R. Huisgen, W. Mack, and L. Möbius, Tetrahedron 9, 29 (1960).Google Scholar
  653. 572.
    M. J. S. Dewar and W.-K. Li, J. Am. Chem. Soc. 96, 5569 (1974).Google Scholar
  654. 573.
    M. J. S. Dewar and G. P. Ford, Chem. Soc. Chem. Commun., 539 (1977).Google Scholar
  655. 574.
    V. Schomaker and L. Pauling, J. Am. Chem. Soc. 61, 1769 (1939).Google Scholar
  656. 575.
    B. Bäk, D. Christensen, L. Hansen-Nygaard, and J. Rastrup-Andersen, J. Mol. Spectrosc. 7, 58 (1961).ADSGoogle Scholar
  657. 576.
    B. Bäk, D. Christensen, L. Hansen, and J. Rastrup-Andersen, J. Chem. Phys. 24, 720 (1956).ADSGoogle Scholar
  658. 577.
    B. Bäk, D. Christensen, W. B. Dixon, L. Hansen-Nygaard, J. Rastrup-Andersen, and M. Schottlander, J. Mol. Spectrosc. 9, 124 (1962).ADSGoogle Scholar
  659. 578.
    D. Spinelli, G. Guanti, and C. Dell’Erba, J. Heterocycl. Chem. 5, 323 (1968).Google Scholar
  660. 579.
    D. Spinelli, R. Noto, G. Consiglio, and A. Storace, J. Chem. Soc. Perkin Trans. 2, 1805 (1976);Google Scholar
  661. G. Consiglio, S. Gronowitz, A. B. Hörnfeldt, B. Maltesson, R. Noto, and D. Spinelli, Chem. Scr. 11, 175 (1977);Google Scholar
  662. G. Consiglio, S. Gronowitz, A. B. Hörnfeldt, R. Noto, K. Pettersson, and D. Spinelli, Chem. Scr. 13, 20 (1978).Google Scholar
  663. 580.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), pp. 356–357.Google Scholar
  664. 581.
    L. K. Montgomery and L. E. Applegate, J. Am. Chem. Soc. 89, 5305 (1967).Google Scholar
  665. 582.
    L. K. Montgomery, F. Scardiglia, and J. D. Roberts, J. Am. Chem. Soc. 87, 1917 (1965).Google Scholar
  666. 583.
    R. L. Hillard III and K. P. C. Vollhardt, J. Am. Chem. Soc. 98, 3579 (1976).Google Scholar
  667. 584.
    G. Eigenmann and H. Zollinger, Helv. Chim. Acta 48, 1795 (1965).Google Scholar
  668. 585.
    G. Wittig and H. Heyn, Chem. Ber. 97, 1609 (1964).Google Scholar
  669. 586.
    J. Bolster and R. M. Kellogg, to be published, cited in J. Bolster and R. M. Kellogg, J. Org. Chem. 45, 4804 (1980). J. Am. Chem. Soc. 103, 2868 (1981) have recently reported the generation of a derivative of 20 (X=S).Google Scholar
  670. 587.
    E. H. Rodd, Ed., Chemistry of Carbon Compounds, Vol. HIB, Elsevier Publishing, New York (1956), Chaps. XX, XXI, and XXII.Google Scholar
  671. 588.
    A. Banerji, J. C. Cass, and A. R. Katritzky, J. Chem. Soc. Perkin Trans. 1, 1162 (1977).Google Scholar
  672. 589.
    R. W. Hoffmann, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967), p. 290.Google Scholar
  673. 590.
    H. E. Zieger and G. Wittig, J. Org. Chem. 27, 3270 (1962).Google Scholar
  674. 591.
    G. Wittig and R. W. Bashe, in preparation, cited in G. Wittig and M. Rings, Justus Liebigs Ann. Chem. 719, 127 (1968), footnote 27.Google Scholar

Copyright information

© Plenum Press, New York 1982

Authors and Affiliations

  • Manfred G. Reinecke
    • 1
  1. 1.Department of ChemistryTexas Christian UniversityFort WorthUSA

Personalised recommendations