Diels-Alder Reaction

  • B. C. Trivedi
  • B. M. Culbertson

Abstract

In this chapter, we will consider the one reaction of maleic anhydride that has been most investigated in the last half-century. Of historical significance is the formation of a cyclohexene derivative 3 from a conjugated diene (butadiene) 2 and a dienophile (maleic anhydride, MA) 1 as reported by Otto Diels and Kurt Alder in 1928.(1)* This reaction is called the Diels-Alder (DA) reaction, diene synthesis, or the [4 + 2] cycloaddition reaction. The role that MA has played in this reaction along with other dienophiles cannot possibly be covered in a single chapter such as this. The impetus it provided to synthetic organic research, particularly in the fields of steroids, polycyclic aromatics, and alkaloids, by allowing a one-step ring closure, can barely be exemplified in a treatment such as this. The efforts of Diels and Alder were duly recognized by a Nobel Prize for chemistry in 1950.(2)

Keywords

High Occupied Molecular Orbital Lower Unoccupied Molecular Orbital Maleic Anhydride Fumaric Acid Adduct Formation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    O. Diels and K. Alder, Justus Liebigs Ann. Chem. 460, 98 (1928).Google Scholar
  2. 2.
    Chem. Eng. News 28, 4266 (1950).Google Scholar
  3. 3.
    S. S. Gutkin, Fed. Paint Varnish Prod. Club Official Digest 317, 371 (1951).Google Scholar
  4. 4.
    T. F. Bradley, E. L. Kropa, and W. B. Johnston, Ind. Eng. Chem. 29(11), 1270 (1937).Google Scholar
  5. 5.
    Unsaturated Polyester Technology, p. 97, P. F. Bruins, ed., Gordon and Breach, New York (1976).Google Scholar
  6. 6.
    L. H. Flett and W. H. Gardner, Maleic Anhydride Derivatives, Wiley, New York (1952).Google Scholar
  7. 7.
    L. W. Butz, A. M. Gaddis, E. W. J. Poutz, and R. E. Davin, J. Org. Chem. 5, 379 (1940).Google Scholar
  8. 8.
    A. Wasserman, Diels-Alder Reactions, Elsevier, Amsterdam (1965).Google Scholar
  9. 9.
    W. Bergmann and F. Hirschmann, J. Org. Chem. 4, 40 (1939).Google Scholar
  10. 10.
    J. Berchet and W. H. Carothers, J. Am. Chem. Soc. 55, 2004 (1933).Google Scholar
  11. 11.
    D. Craig, J. J. Shipman, and R. B. Fowler, J. Am. Chem. Soc. 83, 2885 (1961).Google Scholar
  12. 12.
    J. A. Norton, Chem. Rev. 31, 379 (1942).Google Scholar
  13. 13.
    H. Jahor and P. Goetzky, Z. Chem. 2, 311 (1962).Google Scholar
  14. 14.
    H. J. Backer, Rec. Tray. Chem. 58, 643 (1939).Google Scholar
  15. 15.
    C. F. H. Allen, E. G. Elliot, and A. Ball, Can. J. Res. B 17, 75 (1939).Google Scholar
  16. 16.
    D. Craig, J. Am. Chem. Soc. 65, 1006 (1943).Google Scholar
  17. 17.
    F. C. Carey and A. C. Court, J. Org. Chem. 37, 4474 (1972).Google Scholar
  18. 18.
    O. Grummit and F. J. Christoph, J. Am. Chem. Soc. 73, 3479 (1951).Google Scholar
  19. 19.
    W. G. Bickford, E. F. DuPre, C. H. Mack, and R. T. O’Connor, J. Am. Oil Chem. Soc., 376 (1953).Google Scholar
  20. 20.
    C. Chin, J. Chem. Soc. Jap. Ind. Chem. Soc. 53, 333 (1950).Google Scholar
  21. 21.
    R. S. Morrell and W. R. Davis, Trans. Faraday Soc. 32, 209 (1936).Google Scholar
  22. 22.
    R. Kuhn and T. Wagner-Jauregg, Ber. 63B, 2662 (1930).Google Scholar
  23. 23.
    M. C. Kloetzel, Organic Reactions, Vol. 4, Chap. 1, p. 13, R. Adams, et al., eds., Wiley, New York (1948).Google Scholar
  24. 24.
    K. Alder and O. Ackermann, Chem. Ber. 87, 1567 (1954).Google Scholar
  25. 25.
    U. Modlhammer and H. Hopf, Angew. Chem. (Int. Ed. Engl.) 14(7), 501 (1975).Google Scholar
  26. 26.
    E. E. Gruber and R. R. Adams, J. Am. Chem. Soc. 57, 2555 (1935).Google Scholar
  27. 27.
    F. Bergmann, J. Am. Chem. Soc. 60, 2811 (1938).Google Scholar
  28. 28.
    H. R. Snyder, H. A. Kornberg, and J. R. Ronig, J. Am. Chem. Soc. 61, 3558 (1939).Google Scholar
  29. 29.
    H. R. Snyder and J. C. Robinson, Jr., J. Am. Chem. Soc. 63, 3279 (1941).Google Scholar
  30. 30.
    O. Nicodemus, H. Vollmann, and F. Schloffer (to I. G. Farbenind A.G.), Ger. Pat. 715,201 (1941).Google Scholar
  31. 31.
    H. Meerwin, H. Adam, and H. Buchoch, J. Prakt. Chem. 147, 224 (1936).Google Scholar
  32. 32.
    E. Berner, Acta Chem. Scand. 10, 268 (1956).Google Scholar
  33. 33.
    S. M. Mellows and P. G. Sammes, Chem. Commun., 21 (1971).Google Scholar
  34. 34.
    F. Nerdel and W. Brodowski, Chem. Ber. 101, 1398 (1968).Google Scholar
  35. 35.
    B. I. Ardashev and Z. D. Markova, J. Gen. Chem. USSR 21, 1645 (1951).Google Scholar
  36. 36.
    K. N. Zelenin, V. A. Nikitin, N. M. Anodina, and Z. M. Matveeva, Zh. Org. Khim. 8(7), 1438 (1972).Google Scholar
  37. 37.
    M. P. Cava and M. J. Mitchell, J. Am. Chem. Soc. 81, 5409 (1959).Google Scholar
  38. 38.
    K. Alder, S. Harting, and G. Hausmann, Chem. Ber. 89, 1972 (1956).Google Scholar
  39. 39.
    K. Alder and H. H. Molls, Chem. Ber. 89, 1960 (1956).Google Scholar
  40. 40.
    E. P. Kohler, M. Tishler, H. Potter, and H. T. Thompson, J. Am. Chem. Soc. 61, 1057 (1939).Google Scholar
  41. 41.
    J. D. Roberts and M. C. Casserio, Basic Principles of Organic Chemistry, p. 266, Benjamin, New York (1965).Google Scholar
  42. 42.
    K. Alder and E. Windermuth, Liebigs Ann. Chem. 543, 56 (1940).Google Scholar
  43. 43.
    K. Alder and H. Holzrichter, Liebigs Ann. Chem. 524, 145 (1936).Google Scholar
  44. 44.
    N. L. Drake and J. R. Adam, Jr., J. Am. Chem. Soc. 61, 1326 (1939).Google Scholar
  45. 45.
    E. A. Prill, J. Am. Chem. Soc. 69, 62 (1947).Google Scholar
  46. 46.
    V. F. Mironov, T. K. Gar, and L. A. Leites, Izv. Akad. Nauk SSSR Okd. Khim. Nauk., 1387 (1962).Google Scholar
  47. 47.
    M. S. Solakhov, M. M. Guseimov, and E. M. Ismailova, Uch. Zap. Azerb. Univ. Ser. Khim. Nauk 3, 94 (1970);Google Scholar
  48. 47a.
    M. S. Solakhov, M. M. Guseimov, and E. M. Ismailova, Chem. Abstr. 76, 112–771c (1972).Google Scholar
  49. 48.
    E. Vogel and E. G. Wyes, Angew. Chem. (Int. Ed. Engl.) 1, 404 (62).Google Scholar
  50. 49.
    W. Dilthey, W. Schommer, and O. Trosken, Ber. Dtsch. Chem. Ges. 66, 1627 (1933).Google Scholar
  51. 50.
    W. Dilthey, I. Thewalt, and O. Trosken, Ber. Dtsch. Chem. Ges. 67, 1959 (1934).Google Scholar
  52. 51.
    A. I. Konovalov, Y. D. Samuilov, E. A. Berdnikuv, and V. V. Plemenkov, Dokl. Akad. Nauk SSSR 208(4), 862 (1973).Google Scholar
  53. 52.
    O. Diels and K. Alder, Ber. Dtsch. Chem. Ges. 62, 2081 (1929).Google Scholar
  54. 53.
    K. Alder and W. Trimborn, Liebigs Ann. Chem. 566, 58 (1950).Google Scholar
  55. 54.
    E. P. Kohler and J. Kable, J. Am. Chem. Soc. 57, 917 (1935).Google Scholar
  56. 55.
    J. H. Day, Chem. Rev. 53, 167 (1953).Google Scholar
  57. 56.
    P. Wilder and A. Winston, J. Am. Chem. Soc. 77, 5598 (1955).Google Scholar
  58. 57.
    R. B. Woodward and H. Baer, J. Am. Chem. Soc. 66, 645 (1944).Google Scholar
  59. 58.
    K. Alder and R. Ruhrmann, Liebigs Ann. Chem. 566, 1 (1950).Google Scholar
  60. 59.
    D. Craig, J. J. Shipman, J. Kiehl, F. Widmer, R. Fowler, and A. Hawthorne, J. Am. Chem. Soc. 76. 4573 (1954).Google Scholar
  61. 60.
    E. H. Farmer and F. L. Warren, J. Chem. Soc., 827 (1929).Google Scholar
  62. 61.
    K. Alder, “The Diene Synthesis” in: Newer Methods of Preparative Organic Chemistry, Vol. 1, 381–511, Interscience, New York (1948).Google Scholar
  63. 62.
    R. M. Gascoigne, J. Proc. R. Soc. N. S. Wales 74, 359 (1941).Google Scholar
  64. 63.
    M. Lipp and H. Steinbrink, J. Prakt. Chem. 149, 107 (1937).Google Scholar
  65. 64.
    D. S. Matteson and R. A. Davis, Inorg. Chem. 13(4), 859 (1974).Google Scholar
  66. 65.
    K. Alder and H. H. Molls, Chem. Ber. 89, 1960 (1956).Google Scholar
  67. 66.
    E. P. Kohler, M. Tishler, H. Potter, and H. T. Thompson, J. Am. Chem. Soc. 61, 1057 (1939).Google Scholar
  68. 67.
    K. Alder and G. Jacobs, Chem. Ber. 86, 1528 (1953).Google Scholar
  69. 68.
    H. Ishitobi, H. Tanida, K. Tori, and T. Tsuji, Bull. Chem. Soc. Jap. 44, 2993 (1971).Google Scholar
  70. 69.
    W. E. Doering and L. H. Knox, J. Am. Chem. Soc. 75, 297 (1953).Google Scholar
  71. 70.
    T. Nozoe, S. Sato, and T. Ikamo, Proc. Jap. Acad. 27, 655 (1951).Google Scholar
  72. 71.
    I. Saito, Y. Watanabe, and I. Sho, Tetrahedron Lett., 3049 (1977).Google Scholar
  73. 72.
    E. Vogel, R. Schubart, and W. A. Boll, Angew. Chem. (Int. Ed. Engl.) 3, 510 (1964).Google Scholar
  74. 73.
    E. Vogel, W. A. Boll, and H. Gunther, Tetrahedron Lett.. 609 (1965).Google Scholar
  75. 74.
    A. C. Cope, A. C. Haven, F. L. Ramp, and E. R. Trumbull, J. Am. Chem. Soc. 74, 4867 (1952).Google Scholar
  76. 75.
    M. Avram, G. Makteescu, and S. D. Nenitzescu, Liebigs Ann. Chem. 636, 174 (1960).Google Scholar
  77. 76.
    T. Nozoe, T. Mukai, K. Takase, and T. Nagase, Proc. Jap. Acad. 28, 477 (1952).Google Scholar
  78. 77.
    J. G. Martin and R. K. Hill, Chem. Rev. 61, 537 (1961).Google Scholar
  79. 78.
    J. Sauer, Angew. Chem. (Int. Ed. Engl.) 5, 211 (1966).Google Scholar
  80. 79.
    M. F. Bartlett, S. K. Figdor, and K. Wiesner, Can. J. Chem. 30, 291 (1952).Google Scholar
  81. 80.
    R. B. Ingraham, D. M. MacDonald, and K. Wiesner, Can. J. Chem. B 28, 453 (1950).Google Scholar
  82. 81.
    B. J. F. Hudson and R. Robinson, J. Chem. Soc., 715 (1941).Google Scholar
  83. 82.
    G. Bruchner, Ber. Dtsch. Chem. Ges. 75B. 2034 (1942).Google Scholar
  84. 83.
    K. Alder, R. Schmitz-Josten, H. Broockmann, K. Huhn, and H. Gabler, Justus Liebigs Ann. Chem. 585, 1 (1955).Google Scholar
  85. 84.
    M. Zadra and J. J. Tazuna (to Goodyear Tire & Rubber Co.). U.S. Pat. 4.098,718 (1978).Google Scholar
  86. 85.
    T. Wager-Jauregg, Liebigs Ann. Chem. 491, 1 (1931).Google Scholar
  87. 86.
    K. Alder, F. Pascher, and H. Vagt, Ber. Dtsch. Chem. Ges. 75, 1501 (1942).Google Scholar
  88. 87.
    W. R. Roth, Tetrahedron Lett., 1009 (1964).Google Scholar
  89. 88.
    N. Isaacs, Can. J. Chem. 44(3), 415 (1966).Google Scholar
  90. 89.
    J. A. Berson and G. B. Aspelin, Tetrahedron 20, 2697 (1964).Google Scholar
  91. 90.
    A. Cohen, Nature 136, 869 (1935).Google Scholar
  92. 91.
    A. Cohen and F. L. Warren, J. Chem. Soc. 70, 1462 (1948).Google Scholar
  93. 92.
    W. E. Bachmann and L. B. Scott. J. Am. Chem. Soc. 70. 1462 (1948).Google Scholar
  94. 93.
    W. E. Bachmann and J. M. Chemerda, J.. Am. Chem. Soc. 70, 1468 (1948).Google Scholar
  95. 94.
    W. E. Bachmann and M. C. Kloetzel, J.. Am. Chem. Soc. 60, 2204 (1938).Google Scholar
  96. 95.
    V. Bruckner and J. Kovacs, J. Org. Chem. 13, 641 (1948).Google Scholar
  97. 96.
    V. Bruckner, J. Kovacs, and P. Huhn, J. Org. Chem. 16, 1649 (1951).Google Scholar
  98. 97.
    R. C. Cookson and N. S. Wariyar, Chem. Ind. (London), 915 (1955).Google Scholar
  99. 98.
    R. C. Cookson and N. S. Wariyar, Chem. Ind. (London), 327 (1957).Google Scholar
  100. 99.
    K. Takeda and K. Kitahonoki, J. Pharm. Soc. Jap. 73, 280 (1953).Google Scholar
  101. 100.
    W. H. Johns, D. Mangold, and H. Pleiniger, Tetrahedron 18, 267 (1962).Google Scholar
  102. 101.
    M. C. Kloetzel and H. L. Herzog, H. Am. Chem. Soc. 72, 1991 (1950).Google Scholar
  103. 102.
    B. J. Abadir, J. W. Cook, and D. T. Gibson, J. Chem. Soc., 8 (1953).Google Scholar
  104. 103.
    A. Oku, Y. Ohnishi, and F. Mashi, J. Org. Chem. 37, 42–64 (1972).Google Scholar
  105. 104.
    N. S. Wariyar, Indian Acad. Sci. A 43, 231 (1956).Google Scholar
  106. 105.
    K. Takeda, S. Nagakura, and K. Kitahonoki, Pharm. Bull. 1, 135 (1953).Google Scholar
  107. 106.
    B. Danayer (to UCB, SA), W. Ger. Pat. 2,233,767 (1973).Google Scholar
  108. 107.
    G. R. Wilkinson (to Johnson Pinchin Ltd.), Brit. Pat. 572,455 (1945).Google Scholar
  109. 108.
    E. Vogel and R. D. Roth, Angew. Chem. (Int. Ed. Engl.) 3, 228 (1964).Google Scholar
  110. 109.
    W. E. Bachmann and M. C. Kloetzel, J. Am. Chem. Soc. 60, 481 (1938).Google Scholar
  111. 110.
    J. W. Cook and L. Hunter, J. Chem. Soc., 4109 (1953).Google Scholar
  112. 111.
    F. Kaplan and H. Conroy, J. Org. Chem. 28, 1593 (1963).Google Scholar
  113. 112.
    E. Clar, Ber. 64, 2194 (1931).Google Scholar
  114. 113.
    W. E. Bachmann, J. Org. Chem. 3, 434 (1938).Google Scholar
  115. 114.
    W. E. Bachmann and W. Cole, J. Org. Chem. 4, 60 (1939).Google Scholar
  116. 115.
    R. N. Jones, C. J. Gogek, and R. W. Sharpe, Can. J. Res. 26, 719 (1948).Google Scholar
  117. 116.
    E. Clar and F. Clar, Tetrahedron 29, 3267 (1973).Google Scholar
  118. 117.
    W. C. Herndon, J. Chem. Soc. Chem. Commun., 817 (1977).Google Scholar
  119. 118.
    O. Diels, K. Alder, and E. Naujoks, Ber. 62, 554 (1929).Google Scholar
  120. 119.
    O. Diels and S. Olsen, J. Prakt. Chem. 156, 285 (1940).Google Scholar
  121. 120.
    D. Biloric, Croat. Chem. Acta 38, 293 (1966).Google Scholar
  122. 121.
    R. Paul, Bull. Soc. Chim. Fr. 10(5), 163 (1943).Google Scholar
  123. 122.
    R. Paul, C. R. Acad. Sci. (Paris), 208, 1028 (1939).Google Scholar
  124. 123.
    D. Dufraise and R. Prior, Bull. Soc. Chim. Fr. 5(5), 502 (1938).Google Scholar
  125. 124.
    R. Weiss, A. Abeles, and E. Knapp, Monatsch. Chem. 61, 162 (1932).Google Scholar
  126. 125.
    F. Bergmann, J.. Chem. Soc., 1147 (1938).Google Scholar
  127. 126.
    E. B. Barnett, J. Chem. Soc., 1328 (1935).Google Scholar
  128. 127.
    R. Adams, T. A. Geissman, J. Am. Chem. Soc. 61, 2083 (1939).Google Scholar
  129. 128.
    R. Adams and M. H. Gold, J. Am. Chem. Soc. 62, 56 (1940).Google Scholar
  130. 129.
    R. Adams and R. B. Wearn, J. Am. Chem. Soc. 62, 1233 (1940).Google Scholar
  131. 130.
    M. G. Van Campen Jr. and J. R. Johnson, J. Am. Chem. Soc. 55, 430 (1933).Google Scholar
  132. 131.
    S. M. Sherlin, A. Y. Berlin, T. A. Serebrannibera, and F. E. Rabinovich, J. Gen. Chem. USSR 8, 7 (1938);Google Scholar
  133. 131a.
    S. M. Sherlin, A. Y. Berlin, T. A. Serebrannibera, and F. E. Rabinovich, Chem. Abstr. 32, 5397 (1938).Google Scholar
  134. 132.
    K. Alder and C. H. Schmidt, Ber. 76, 183 (1943).Google Scholar
  135. 133.
    O. Diels, K. Alder, W. Lubbert, E. Naujoks, F. Querberitz, K. Rohl, and H. Segeberg, Ann. 470, 62 (1929).Google Scholar
  136. 134.
    O. Diels, K. Alder, and D. Winter, Ann. 486, 211 (1931).Google Scholar
  137. 135.
    O. Diels, K. Alder, H. Winckler, and E. Peterson, Ann. 498, 1 (1932).Google Scholar
  138. 136.
    H. Hopff and C. W. Rautenstrauch (to I. G. Farbenind. A.G.), U.S. Pat. 2,262,002 (1942).Google Scholar
  139. 137.
    L. Mandell and H. A. Blanchard, J.. Am. Chem. Soc. 79, 5198 (1957).Google Scholar
  140. 138.
    R. A. Acheson and J. M. Vernon, J. Chem. Soc., 1148 (1962).Google Scholar
  141. 139.
    R. A. Acheson and J. M. Vernon, J. Chem. Soc., 457 (1961).Google Scholar
  142. 140.
    N. W. Gabel, J. Org. Chem. 27, 301 (1962).Google Scholar
  143. 141.
    L. Mandell, J. V. Piper, and C. E. Pesterfield, J. Org. Chem. 28, 574 (1963).Google Scholar
  144. 142.
    A. H. Kotsuki, S. Kitagawa, H. Nishizawa, and T. Tokoroyama, J. Org. Chem. 43, 1471 (1978).Google Scholar
  145. 143.
    J. M. Baker, P. R. Huddleston, and S. W. Shutler, J. Chem. Soc. Perkin Trans. 1, 2483 (1975).Google Scholar
  146. 144.
    J. Szmuszkovicz and E. J. Modest, J. Am. Chem. Soc. 72, 571 (1950).Google Scholar
  147. 145.
    D. B. Clapp, J. Am. Chem. Soc. 61, 2733 (1939).Google Scholar
  148. 146.
    C. F. H. Allen and J. W. Gates, J. Am. Chem. Soc., 65, 1283 (1943).Google Scholar
  149. 147.
    Y. L. Danyushevskii, M. A. Marakatkina, and Y. L. Goldfarb, Zh. Org. Khim., 4, 474 (1968).Google Scholar
  150. 148.
    H. J. Backer and T. A. H. Blass, Rec. Tray. Chim. 61, 785 (1942).Google Scholar
  151. 149.
    J. L. Melles, Rec. Trav. Chim. 71, 869 (1952).Google Scholar
  152. 150.
    J. E. M. Campbell, R. C. Cookson, and M. R. Hocking, Chem. Ind. (London), 359 (1952).Google Scholar
  153. 151.
    B. A. Arbuzov and E. G. Kataev, Dokl. Akad. Nauk SSSR 65, 493 (1949).Google Scholar
  154. 152.
    R. Balasubramanian and M. V. George, Tetrahedron 29, 2395 (1973).Google Scholar
  155. 153.
    G. Y. Kondrateva, Khim. Nauki. Prom. 2, 666 (1957).Google Scholar
  156. 154.
    G. Y. Kondrateva, Inzvert. Akad. Nauk SSSR Otdel. Khim. Nauk, 484 (1959).Google Scholar
  157. 155.
    T. Matsuo and T. Miki, Chem. Pharm. Bull. 20, 669 (1972).Google Scholar
  158. 156.
    O. Diels, K. Alder, and K. Muller, Ann. 490, 257 (1931).Google Scholar
  159. 157.
    J. Fried and R. C. Elderfield, J. Org. Chem. 6, 566 (1941).Google Scholar
  160. 158.
    H. Hongo, Chem. Pharm. Bull. 20, 226 (1972).Google Scholar
  161. 159.
    I. Sigal and L. Loew, J. Am. Chem. Soc. 100, 394 (1978).Google Scholar
  162. 160.
    E. H. Braye and W. Hubel, Chem. Ind. (London), 1250 (1959).Google Scholar
  163. 161.
    C. K. Bradsher and T. W. G. Soloman, J. Am. Chem. Soc. 80, 933 (1958).Google Scholar
  164. 162.
    A. Schonberg and A. Mustafa, J. Chem. Soc., 654 (1943).Google Scholar
  165. 163.
    C. E. Bird and G. W. H. Cheeseman, J. Chem. Soc., 3037 (1962).Google Scholar
  166. 164.
    E. C. Taylor and E. Smakulka Hand, J. Org. Chem. 27, 3734 (1962).Google Scholar
  167. 165.
    E. C. Taylor and E. Smakulka Hand, Tetrahedron Lett., 1225 (1962).Google Scholar
  168. 166.
    E. C. Taylor and E. Smakulka Hand, J. Am. Chem. Soc. 85, 770 (1963).Google Scholar
  169. 167.
    S. Sarel and E. Breuer, J. Am. Chem. Soc. 81, 6523 (1959).Google Scholar
  170. 168.
    E. F. Ullman, Chem. Ind. (London), 1173 (1958).Google Scholar
  171. 169.
    Z. W. Wicks, O. W. Daly, and H. Lark, J. Org. Chem. 12, 713 (1947).Google Scholar
  172. 170.
    D. Craig and J. J. Shipman, J. Am. Chem. Soc. 74, 2905 (1952).Google Scholar
  173. 171.
    K. Alder and G. Stein, Angew. Chem. 50, 510 (1937).Google Scholar
  174. 172.
    R. B. Woodward and C. J. Baer, J. Am. Chem. Soc. 70, 1161 (1948).Google Scholar
  175. 173.
    F. A. L. Anet, Tetrahedron Lett., 1219 (1962).Google Scholar
  176. 174.
    M. W. Lee and W. C. Herndon, J. Org. Chem. 43, 518 (1978).Google Scholar
  177. 175.
    A. C. Cope, E. Ciganek, and N. A. LaBel, J. Am. Chem. Soc. 81, 2799 (1959).Google Scholar
  178. 176.
    E. H. Farmer and F. L. Warren, J. Chem. Soc., 1809 (1929).Google Scholar
  179. 177.
    K. Alder and H. Vagt, Ann. 591, 153 (1951).Google Scholar
  180. 178.
    J. A. Berson, J. Am. Chem. Soc. 84, 297 (1962).Google Scholar
  181. 179.
    T. Inukai and T. Kojima, J. Org. Chem. 31, 2032 (1966).Google Scholar
  182. 180.
    E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York (1962).Google Scholar
  183. 181.
    J. Sauer, Angew. Chem. (Int. Ed. Engl.) 6, 16 (1967).Google Scholar
  184. 182.
    W. C. Herndon, Chem. Rev., 157 (1972).Google Scholar
  185. 183.
    D. Craig, J. J. Shipman, J. Diehl, F. Widmer, R. Fowler, and A. Hawthorne, J. Am. Chem. Soc. 76, 4573 (1954).Google Scholar
  186. 184.
    S. Seltzer, J.. Am. Chem. Soc. 85, 1360 (1963).Google Scholar
  187. 185.
    S. Seltzer, J. Am. Chem. Soc. 87, 1534 (1965).Google Scholar
  188. 186.
    D. Gagnaire and E. Payo-Subiza, Bull. Soc. Chim. Fr., 2658 (1965).Google Scholar
  189. 187.
    W. Shih, N. Lau, and S. Seltzer, J. Org. Chem. 40, 1269 (1975).Google Scholar
  190. 188.
    D. E. Van Sickle and J. O. Roden, J. Am. Chem. Soc. 86, 3091 (1964).Google Scholar
  191. 189.
    K. F. Wong and C. A. Eckert, Trans. Faraday Soc. 66, 2313 (1970).Google Scholar
  192. 190.
    R. A. Grieger and C. A. Eckert, Am. Inst. Chem. Eng. J. 16, 766 (1970).Google Scholar
  193. 191.
    R. A. Grieger and C. A. Eckert, J. Am. Chem. Soc. 92, 7149 (1970).Google Scholar
  194. 192.
    R. A. Grieger and C. A. Eckert, Trans. Faraday Soc. 66, 2579 (1970).Google Scholar
  195. 193.
    J. R. McCabe and C. A. Eckert, Ind. Eng. Chem. Fundamentals 13, 168 (1974).Google Scholar
  196. 194.
    T. Axano and W. J. LeNoble, Chem. Rev. 78, 407 (1978).Google Scholar
  197. 195.
    E. J. Dewitt, C. T. Lester, and G. A. Ropp, J. Am. Chem. Soc. 78, 2101 (1956).Google Scholar
  198. 196.
    Y. Okamoto and H. C. Brown, J. Org. Chem. 22, 485 (1957).Google Scholar
  199. 197.
    D. N. Matthews and E. I. Becker, J. Org. Chem. 31, 1135 (1966).Google Scholar
  200. 198.
    J. A. Berson and A. Remanick, J. Am. Chem. Soc. 83, 4947 (1961).Google Scholar
  201. 199.
    J. A. Berson and W. A. Mueller, J. Am. Chem. Soc. 83, 4940 (1961).Google Scholar
  202. 200.
    L. J. Andrews and R. M. Keefer, J. Am. Chem. Soc. 77, 6284 (1955).Google Scholar
  203. 201.
    V. D. Kieser and A. I. Konovalov, Zh. Org. Khim. 10, 6 (1974).Google Scholar
  204. 202.
    R. B. Woodward and T. J. Katz, Tetrahedron 5, 70 (1959).Google Scholar
  205. 203.
    R. B. Woodward and R. Hoffman, J. Am. Chem. Soc. 87, 395 (1965).Google Scholar
  206. 204.
    R. Hoffmann and R. B. Woodward, J. Am. Chem. Soc. 87, 4388 (1965).Google Scholar
  207. 205.
    W. J. Bailey and E. W. Cummins, J.. Am. Chem. Soc. 76, 1936 (1954).Google Scholar
  208. 206.
    D. R. Eckroth, J. Org. Chem. 41, 294 (1976).Google Scholar
  209. 207.
    M. T. H. Liu and C. Schmidt, Tetrahedron 27, 5289 (1971).Google Scholar
  210. 208.
    M. Taagepera and E. R. Thornton, J. Am. Chem. Soc. 94, 1188 (1972).Google Scholar
  211. 209.
    K. N. Houk, Acc. Chem. Res. 8, 361 (1975).Google Scholar
  212. 210.
    K. L. Mok and M. J. Nye, J. Chem. Soc. Perkin, I 1810 (1975).Google Scholar
  213. 211.
    P. V. Alston and R. M. Ottenbrite, J. Org. Chem. 39, 1584 (1974).Google Scholar
  214. 212.
    W. E. Bachmann and N. C. Deno, J. Am. Chem. Soc. 71, 3062 (1949).Google Scholar
  215. 213.
    J. Sauer and H. Weist, Angew. Chem. (Int. Ed. Engl.) 1, 269 (1962).Google Scholar
  216. 214.
    R. B. Woodward, J. Am. Chem. Soc. 64, 3058 (1942).Google Scholar
  217. 215.
    P. Yates and P. Eaton, J. Am. Chem. Soc. 82, 4436 (1960).Google Scholar
  218. 216.
    N. T. Anh and J. Seyden-Penne, Tetrahedron 29, 3259 (1973).Google Scholar
  219. 217.
    M. Augustin and M. Kohler, Wissen. Z. Martin Luther Univ. Halle-Wittenberg, Math.-Naturwiss. Reihe 25, 5 (1976).Google Scholar
  220. 218.
    J. L. Rifoll, A. Rouessac, and F. Rouessac, Tetrahedron 34, 3 (1978).Google Scholar
  221. 219.
    R. F. Robey, Science 96, 470 (1942).Google Scholar
  222. 220.
    E. Clar, Ber. 65, 846 (1932).Google Scholar
  223. 221.
    G. McMulen, G. Sedelmeier, R. Hildebrand, H. Fritz, and H. Prinzbach, Tetrahedron Lett., 3847 (1979).Google Scholar
  224. 222.
    A. F. Murad, J. Kleinschroth, and H. Hopf, Angew. Chem. (Int. Ed. Engl.) 19(5), 389 (1980).Google Scholar
  225. 223.
    K. Naito and B. Rickborn, J. Org. Chem. 45, 4061 (1980).Google Scholar
  226. 224.
    H. Tomisawa, H. Hongo, R. Fujita, and H. Kato, Heterocycles 6, 1765 (1977).Google Scholar
  227. 225.
    F. W. Harris, B. A. Reinhardt, R. D. Case, and W. A. Feld, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 19(1), 556 (1978).Google Scholar
  228. 226.
    R. L. Danheiser and H. Sard, J. Org. Chem. 45, 4810 (1980).Google Scholar
  229. 227.
    T. Wagner-Jauregg, Synthesis, 769 (1980).Google Scholar
  230. 228.
    W. E. Noland, V. Kameswaran, and L. L. Landucci, J. Org. Chem. 45, 4565 (1980).Google Scholar
  231. 229.
    A. B. Whiting, NTIS Report (1979). Order No. AD-A077581. See Chem. Abstr. 93, 150065j (1980).Google Scholar
  232. 230.
    M. C. Bohm, R. V. C. Carr, R. Gleiter, and L. A. Paquette, J. Am. Chem. Soc. 102, 7218 (1980).Google Scholar
  233. 231.
    P. X. Iten, A. A. Hofmann, and C. H. Eugster, Helv. Chim. Acta 62, 2202 (1979).Google Scholar
  234. 232.
    J. Sauer and R. Sustmann, Angew. Chem. (Int. Ed. Engl.) 19, 779 (1980).Google Scholar
  235. 233.
    D. Biermann and W. Schmidt, J. Am. Chem. Soc. 102 3163 (1980)Google Scholar
  236. 234.
    D. Biermann and W. Schmidt, J. Am. Chem. Soc. 102, 3173 (1980).Google Scholar
  237. 235.
    A. Mielert, C. Braig, J. Sauer, J. Martelli, and R. Sustmann, Justus Liebigs Ann. Chem. 6, 954 (1980).Google Scholar

Copyright information

© Springer Science+Business Media New York 1982

Authors and Affiliations

  • B. C. Trivedi
    • 1
  • B. M. Culbertson
    • 1
  1. 1.Ashland Chemical CompanyDublinUSA

Personalised recommendations