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Thermal and photochemical 1,3-electrocyclic reactions in the chemistry of three-membered heterocyclic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Recent data on thermal and photochemical 1,3-electrocyclic reactions are examined and systematized.

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Literature Cited

  1. R. B. Woodward and R. Hoffmann, The Retention of Orbital Symmetry [Russian translation], Mir, Moscow (1971), p. 206.

    Google Scholar 

  2. E. N. Marvell, Thermal Electrocyclic Reactions, Interscience, New York (1980), p. 503.

    Google Scholar 

  3. J. S. Burnier and W. L. Jorgensen, J. Org. Chem., 49, 3001 (1984).

    Google Scholar 

  4. P. G. Gassman and C. K. Harrington, J. Org. Chem., 49, 2258 (1984).

    Google Scholar 

  5. A. V. Koblik and K. F. Suzdalev, Zh. Org. Khim., 18, 1778 (1982).

    Google Scholar 

  6. A. M. Moiseenkov, B. A. Czeskiks, T. Y. Rudashevskaya, and A. V. Nesmeyanova, Tetrahedron Lett., 22., 151 (1981).

    Google Scholar 

  7. P. R. Schleyer and M. Bremer, J. Org. Chem., 53, 2362 (1988).

    Google Scholar 

  8. M. H. Lien and A. C. Hopkinson, J. Am. Chem. Soc., 110, 3788 (1988).

    Google Scholar 

  9. F. Turecek and F. W. McLafferty, Org. Mass Spectrom., 18, 608 (1983).

    Google Scholar 

  10. J. K. Terlouw, W. Heerma, and J. L. Holmes, Org. Mass Spectrom., 16, 307 (1981).

    Google Scholar 

  11. M. Spraul and K. Griesbaum, Chem. Ber., 116, 2641 (1983).

    Google Scholar 

  12. A. P. Marchand, Pericyclic Reactions, Vol. 2, Wiley-Interscience, New York (1977), p. 241.

    Google Scholar 

  13. F. J. Ablenas, B. E. George, M. Maleki, R. Jain, A. C. Hopkinson, and E. Lee-Ruff, Can. J. Chem., 65, 1800 (1987).

    Google Scholar 

  14. G. L'Abbe, Angew. Chem., No. 4, 277 (1980).

    Google Scholar 

  15. T. H. Chan and B. S. Ong, Tetrahedron, 36, 2269 (1980).

    Google Scholar 

  16. E. Block, R. E. Penn, M. D. Ennis, T. A. Owens, and S. L. Yu, J. Am. Chem. Soc., 100, 7436 (1978).

    Google Scholar 

  17. W. Ando, Y. Hanyu, T. Furuhata, and T. Takata, J. Am. Chem. Soc., 105, 6151 (1983).

    Google Scholar 

  18. R. W. Saalfrahk, W. Paul, P. Schierling, H. Schüler, and E. Wilhelm, Chem. Ber., 115, 57 (1982).

    Google Scholar 

  19. W. Ando, T. Furahata, Y. Hanyu, and T. Takata, Tetrahedron Lett., 25, 4011 (1984).

    Google Scholar 

  20. B. Föhlisch and I. Heerscher, Chem. Ber., 118, 524 (1985).

    Google Scholar 

  21. P. Schrimin, F. D. Angeli, A. C. Veronese, and V. Baioni, Tetrahedron Lett., 24, 4473 (1983).

    Google Scholar 

  22. T. S. Otohiko, Bull. Chem. Soc. Jpn., 59., 2537 (1986).

    Google Scholar 

  23. N. De Kimpe, P. Salmon, R. Verhe, L. De Buyek, and N. Schamp, J. Org. Chem., 48, 4320 (1983).

    Google Scholar 

  24. J. Mann, Tetrahedron, 42, 4611 (1986).

    Google Scholar 

  25. O. Kikuchi, H. Nagata, and K. Morihashi, Theochem., 25, 261 (1985).

    Google Scholar 

  26. L. J. Schaad, B. A. Hess, and R. Zahradnik, J. Org. Chem., 46, 1909 (1981).

    Google Scholar 

  27. R. M. Moriarty, S. C. Gupta, H. Hu, D. R. Berenschot, and K. B. White, J. Am. Chem. Soc., 103, 686 (1981).

    Google Scholar 

  28. R. S. Sagitullin, S. P. Gromov, and A. N. Kost, Dokl. Akad. Nauk SSSR, 236, 634 (1977).

    Google Scholar 

  29. G. L'Abbe and K. Allewaert, Bull. Soc. Chim. Belges., 97, 1 (1988).

    Google Scholar 

  30. A. Padwa, T. J. Blacklock, and R. Losa, J. Org. Chem., 47, 3712 (1982).

    Google Scholar 

  31. M. I. Komendantov, R. R. Bekmukhametov, and I. N. Domnin, Zh. Org. Khim., 14, 759 (1978).

    Google Scholar 

  32. M. I. Komendantov, A. P. Zavgorodnaya, I. N. Domnin, and R. R. Bekmukhametov, Zh. Org. Khim., 22, 1541 (1986).

    Google Scholar 

  33. J. A. Pincock and N. C. Mathur, J. Org. Chem., 47, 3699 (1982).

    Google Scholar 

  34. H. Dürr and L. Schrader, Angew. Chem., Int. Ed. Engl., 8, 446 (1969).

    Google Scholar 

  35. D. L. Boger and C. E. Brotherton, J. Am. Chem. Soc., 108, 6695 (1986).

    Google Scholar 

  36. A. M. Lakshin, I. G. Zenkevich, and I. N. Domnin, Zh. Org. Khim., 22, 1656 (1986).

    Google Scholar 

  37. G. Smolinsky and C. W. Pryde, J. Org. Chem., 32, 2411 (1968).

    Google Scholar 

  38. K. Isomura, S. Noguchi, M. Saruwatari, S. Hatano, and H. Taniguchi, Tetrahedron Lett., 21, 3879 (1980).

    Google Scholar 

  39. A. Gazit and Z. Rappoport, J. Org. Chem., 53, 679 (1988).

    Google Scholar 

  40. H. Bock and R. Dammel, Chem. Ber., 120, 1971 (1987).

    Google Scholar 

  41. B. A. Shainyan and A. N. Mirskova, Zh. Org. Khim., 22, 889 (1986).

    Google Scholar 

  42. R. W. Saalfrank, E. Ackermann, M. Fisher, and U. Wirth, Chem. Ber., 120, 2003 (1987).

    Google Scholar 

  43. T. Nischiwaki, Tetrahedron Lett., 10, 2049 (1969).

    Google Scholar 

  44. D. J. Pasto and J. P. Freeman, J. Am. Chem. Soc., 107, 4090 (1985).

    Google Scholar 

  45. Y. Ohba, I. Matsukura, Y. Fukarawa, and T. Nishiwaki, Heterocycles, 23, 287 (1985).

    Google Scholar 

  46. D. Ranganathan, S. Bamezai, and P. V. Ramachandran, Heterocycles, 23, 623 (1985).

    Google Scholar 

  47. H. Sawanishi, T. Hirai, and T. Tsuchiya, Heterocycles, 22, 1501 (1984).

    Google Scholar 

  48. Y. Ohba, S. Kubo, and T. Nishiwaki, Heterocycles, 22, 457 (1984).

    Google Scholar 

  49. D. Barton and U. D. Ollis (eds.), General Organic Chemistry [Russian translation], Vol. 8, Khimiya, Moscow (1985), p. 710.

    Google Scholar 

  50. Z. U. Khan, D. J. Patel, R. K. Smalley, E. F. V. Scriven, and H. Suschitzky, J. Chem. Soc., Perkin 1, No. 10, 2495 (1983).

    Google Scholar 

  51. C. M. Daly, B. Iddon, H. Suschitzky, U. Jordis, and F. Sauter, J. Chem. Soc., Perkin 1, No. 7, 1933 (1988).

    Google Scholar 

  52. D. J. Patel and P. K. Smalley, J. Chem. Soc., Perkin 1, No. 11, 2587 (1984).

    Google Scholar 

  53. B. A. Trofimov and A. I. Mikhaleva, Khim. Geterotsikl. Soedin., No. 10, 1299 (1987).

    Google Scholar 

  54. E. C. Taylor and I. J. Turchi, Chem. Rev., 79, 181 (1979).

    Google Scholar 

  55. A. Padwa, R. J. Rosenthal, W. Dent, P. Filho, N. J. Turro, D. A. Hrovat, and J. R. Gould, J. Org. Chem., 49, 3174 (1984).

    Google Scholar 

  56. J. D. Perez, R. G. Dinz, and G. I. Yranzo, J. Org. Chem., 46, 3505 (1981).

    Google Scholar 

  57. A. V. Prosyanik, P. N. Belov, and V. I. Markov, Khim. Geterotsikl. Soedin., No. 12, 1688 (1984).

    Google Scholar 

  58. Y. Y. Ko, C. Yenng Lam, R. Carrie, F. DeSarlo, and A. Brandi, Can. J. Chem., 61, 1105 (1983).

    Google Scholar 

  59. A. Padwa, J. R. Gasdaska, G. Hafmanns, and H. Rebello, 52, 1027 (1987).

  60. E. Voigt and H. Meier, Chem. Ber., 108, 3326 (1975).

    Google Scholar 

  61. I. G. Csirmadia, J. Font, and O. P. Strausz, J. Am. Chem. Soc., 90, 7380 (1968).

    Google Scholar 

  62. G. Maier, H. P. Reisenauer, and T. Sayrac, Chem. Ber., 115, 2192 (1982).

    Google Scholar 

  63. R. L. Russel and F. S. Rowland, J. Am. Chem. Soc., 92, 1508 (1970).

    Google Scholar 

  64. V. A. Bakulev and V. S. Mokrushin, Khim. Geterotsikl. Soedin., No. 8, 1011 (1986).

    Google Scholar 

  65. O. Strausz, J. Fount, E. Dedio, P. Kelarle, and H. Gunning, J. Am. Chem. Soc., 89, 4805 (1967).

    Google Scholar 

  66. N. D. A. Walsh, General Organic Chemistry [Russian translation], Vol. 9, Khimiya, Moscow (1985), p. 293.

    Google Scholar 

  67. T. J. Barton and G. C. Paul, J. Am. Chem. Soc., 109, 5292 (1987).

    Google Scholar 

  68. W. Bouma, R. H. Nobes, L. Radom, and C. E. Woodward, J. Org. Chem., 47, 1869 (1982).

    Google Scholar 

  69. I. O. Shapiro and I. A. Mizurkin, Zh. Org. Khim., 22, 2296 (1986).

    Google Scholar 

  70. M. E. M. Attia, Y. Gelas-Mialhe, and R. Vessiere, Can. J. Chem., 61, 2126 (1983).

    Google Scholar 

  71. T. Kametani and T. Honda, Adv. Heterocycl. Chem. 39, 182 (1986).

    Google Scholar 

  72. E. Vedejs, S. Dax, C. R. Martinez, and C. K. McClure, J. Org. Chem., No. 15, 3470 (1987).

    Google Scholar 

  73. E. Vedejs, J. Wisniewski, and J. K. Preston, J. Org. Chem., 52, 3487 (1987).

    Google Scholar 

  74. J. Bougois, A. Mathieu, and F. Texier, J. Heterocycl. Chem., 21, 513 (1984).

    Google Scholar 

  75. P. De Shong and D. A. Kell, Tetrahedron Lett., 27, 3979 (1986).

    Google Scholar 

  76. H. Benhaoua, F. Texier, L. Toupet, and R. Carrier, Tetrahedron, 44, 1117 (1988).

    Google Scholar 

  77. E. Vedejs and J. W. Grissom, J. Org. Chem., 53, 1882 (1988).

    Google Scholar 

  78. A. Padwa, 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York (1980), p. 704.

    Google Scholar 

  79. J. A. Charrier, A. Foucand, H. Person, and E. Lowkakou, J. Org. Chem., 48, 481 (1983).

    Google Scholar 

  80. W. H. Pearson, J. E. Gelebuski, Y. F. Poon, B. R. Dixon, and J. H. Glans, Tetrahedron Lett., 27, 6301 (1986).

    Google Scholar 

  81. J. I. G. Cadogan, C. L. Hickson, and H. McNab, J. Chem. Soc., Perkin 1, No. 9, 1885 (1985).

    Google Scholar 

  82. M. G. Barlow, G. H. Harrison, R. N. Haszeldine, W. D. Morton, P. Show-Luckman, and M. D. Ward, J. Chem. Soc., Perkin 1, No. 9, 2101 (1982).

    Google Scholar 

  83. M. L. M. Penning, D. N. Reinhondt, S. Harkema, and G. J. Van Hummel, J. Org. Chem., 48, 486 (1983).

    Google Scholar 

  84. D. Wenkert, S. B. Ferguson, B. Porter, A. Quarnstrom, and A. T. McPail, J. Org. Chem., 50, 4114 (1985).

    Google Scholar 

  85. R. Bartnik and G. Mloston, Tetrahedron, 40, 2569 (1984).

    Google Scholar 

  86. R. Huisgen, W. Scheer, and H. Huber, J. Am. Chem. Soc., 89, 1753 (1967).

    Google Scholar 

  87. W. Eberbach and J. C. Carrier, Chem. Ber., 116, 563 (1983).

    Google Scholar 

  88. S. C. Kim, Tachan Hwahakhoe Chi, 30, 248 (1986); Chem. Abstr., 106, 17614 (1987).

    Google Scholar 

  89. K. N. Houk, N. G. Rondan, C. Santiago, C. J. Gallo, R. W. Gandour, and G. W. Griffin, J. Am. Chem. Soc., 102, 1504 (1980).

    Google Scholar 

  90. F. Volatron, N. T. Anh, and Y. Jean, J. Am. Chem. Soc., 105, 2359 (1983).

    Google Scholar 

  91. E. F. Hayes and A. K. Q. Siu, J. Am. Chem. Soc., 93, 2091 (1971).

    Google Scholar 

  92. K. Yamaguchi, A. Nischio, S. Yabushita, and T. Fueno, Chem. Lett., No. 12, 1479 (1977).

    Google Scholar 

  93. P. E. Hiberty and C. Leforestier, J. Am. Chem. Soc., 100. 2012 (1978).

    Google Scholar 

  94. H. Hamberger and R. Huisgen, J. Chem. Soc., Chem. Commun., No. 19, 1190 (1971).

    Google Scholar 

  95. V. Markowski and R. Huisgen, J. Chem. Soc., Chem. Commun., No. 13, 439 (1977).

    Google Scholar 

  96. Y. Jean, F. Volatron, and T. A. Nguen, Theochem., 10, 167 (1983).

    Google Scholar 

  97. W. Eberbach and J. C. Carre, Chem. Ber., 114, 1027 (1981).

    Google Scholar 

  98. H. Hart, S.-M. Chen, S. Lee, D. L. Ward, and W.-J. H. Kung, J. Org. Chem., 45, 2091 (1980).

    Google Scholar 

  99. R. Huisgen and P. DeMacch, J. Am. Chem. Soc., 104, 4953 (1982).

    Google Scholar 

  100. R. Huisgen and P. DeMacch, J. Am. Chem. Soc., 104, 4952 (1982).

    Google Scholar 

  101. K. N. Houk, Acc. Chem. Res., 8, 361 (1975).

    Google Scholar 

  102. J. Brokatzky-Geiger and W. Eberbach, Chem. Ber., 116, 2383 (1983).

    Google Scholar 

  103. J. Brokatzky-Geiger and W. Eberbach, Chem. Ber., 114, 384 (1981).

    Google Scholar 

  104. J. Brokatzky-Geiger and W. Eberbach, Chem. Ber., 117, 2157 (1984).

    Google Scholar 

  105. W. Eberbach and U. Trostmann, Chem. Ber., 114, 2979 (1981).

    Google Scholar 

  106. W. Eberbach and U. Trostmann, Chem. Ber., 118, 4035 (1985).

    Google Scholar 

  107. W. Eberbach, W. Seiler, and H. Freitz, Chem. Ber., 113, 875 (1980).

    Google Scholar 

  108. L. E. Manring and K. S. Peters, J. Am. Chem. Soc., 106, 8077 (1984).

    Google Scholar 

  109. G. A. Lee, J. Org. Chem., 43, 4256 (1978).

    Google Scholar 

  110. P. Hallet, J. Muzart, and J. P. Pete, J. Org. Chem., 46, 4275 (1981).

    Google Scholar 

  111. P. Hallet, J. Muzart, and J. P. Pete, Tetrahedron Lett., 20, 2727 (1979).

    Google Scholar 

  112. H. Kato, H. Tezuka, K. Yamaguchi, K. Nowada, and Y. Nakamura, J. Chem. Soc., Perkin 1, No. 9, 1029 (1978).

    Google Scholar 

  113. A. Osuka, J. Org. Chem., 48, 1712 (1983).

    Google Scholar 

  114. A. M. Trozzolo, W. A. Yager, C. W. Griffin, H. Kristinnsson, and I. Karkar, J. Am. Chem. Soc., 89, 3357 (1967).

    Google Scholar 

  115. A. M. Trozzolo, T. M. Leslie, A. S. Sarpotdar, R. D. Small, G. J. Ferrandi, T. Dominh, and R. L. Hartless, Pure Appl. Chem., 51, 261 (1979).

    Google Scholar 

  116. S. N. Ege, A. D. Adams, E. J. Gess, K. S. Ragone, B. J. Kober, N. B. Lampert, P. Umrigar, D. C. Lankin, and G. W. Griffin, J. Chem. Soc., Perkin 1, No. 2, 325 (1983).

    Google Scholar 

  117. I. K. Anokhina,. N. G. Fedorova, L. P. Zalukaev, and M. Yu. Krysin, Khim. Geterotsikl. Soedin., No. 7, 881 (1988).

    Google Scholar 

  118. A. P. Alder, H. R. Wolf, and O. Jeger, Helv. Chim. Acta, 64, 224 (1981).

    Google Scholar 

  119. L. D. Snow, J. T. Wang, and F. Williams, Chem. Phys. Lett., 103, 193 (1983).

    Google Scholar 

  120. X. Z. Qin, L. D. Snow, and F. Williams, J. Am. Chem. Soc., 107, 3366 (1985).

    Google Scholar 

  121. T. Bally, S. Nitsche, and E. Haselbach, Helv, Chim. Acta, 67, 86 (1984).

    Google Scholar 

  122. T. Clark, J. Chem. Soc., Chem. Commun., No. 3, 66 (1984).

    Google Scholar 

  123. R. H. Nobes, W. J. Bouma, J. K. MacLeod, and L. Radom, Chem. Phys. Lett., 135, 78 (1987).

    Google Scholar 

  124. P. Du and W. T. Borden, J. Am. Chem. Soc., 109, 5330 (1987).

    Google Scholar 

  125. R. N. Kellog, Tetrahedron, 32, 2165 (1976).

    Google Scholar 

  126. P. Gronski and K. Hartke, Tetrahedron Lett., 17, 4139 (1976).

    Google Scholar 

  127. R. Huisgen, C. Fulka, I. Kalwinsch, L. Xingya, G. Mloston, J. R. Moran, and A. Pröbstl, Bull. Soc. Chem. Beiges, 93, 511 (1984).

    Google Scholar 

  128. O. Schweikert, T. Netscher, L. Knothe, and H. Prinzbach, Chem. Ber., 117, 2049 (1984).

    Google Scholar 

  129. I. Kalwinsch and R. Huisgen, Tetrahedron Lett., 22, 3941 (1981).

    Google Scholar 

  130. I. Kalwinsch, X. Li, J. Gottstein, and R. Huisgen, J. Am. Chem. Soc., 103, 7032 (1981).

    Google Scholar 

  131. R. Huisgen, G. Mloston, and E. Langhals, J. Am. Chem. Soc., 108, 6401 (1986).

    Google Scholar 

  132. T. B. Cameron and H. W. Pinnick, J. Am. Chem. Soc., 101, 4755 (1979).

    Google Scholar 

  133. T. B. Cameron and H. W. Pinnick, J. Am. Chem. Soc., 102, 744 (1980).

    Google Scholar 

  134. E. M. Lown, K. S. Sidhu, A. W. Jackson, A. Jordan, M. Green, and P. Strauszo, J. Prakt. Chem., 323, 1089 (1981).

    Google Scholar 

  135. X. Li and R. Huisgen, Tetrahedron Lett., 24, 4181 (1983).

    Google Scholar 

  136. R. Huisgen and X. Li, Tetrahedron Lett., 24, 4185 (1983).

    Google Scholar 

  137. R. Huisgen, E. Langhals, and H. Noth, Tetrahedron Lett., 27, 5475 (1986).

    Google Scholar 

  138. H. Gotthardt, W. Pflaumbaum, and P. Gutowski, Chem. Ber., 121, 313 (1988).

    Google Scholar 

  139. R. Huisgen and X. Li, Heterocycles, 20, 2363 (1983).

    Google Scholar 

  140. K. Oka, A. Dobashi, and S. Hara, Tetrahedron Lett., 21, 3579 (1980).

    Google Scholar 

  141. A. Corsaro, A. Compagnini, G. Perrini, and D. Purrello, J. Chem. Soc., Perkin 1, No. 5, 897 (1984).

    Google Scholar 

  142. R. A. Bekker, L. A. Rozov, and F. Ya. Popkova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2575 (1983).

    Google Scholar 

  143. A. P. Krapcho, D. R. Rao, M. P. Silvon, and B. Abegas, J. Org. Chem., 36, 3885 (1971).

    Google Scholar 

  144. D. H. R. Barton, F. S. Gruziec, and K. Shahak, J. Chem. Soc., Perkin 1, No. 6, 1794 (1974).

    Google Scholar 

  145. G. Tomaschewski, U. Klein, and G. Geissler, Tetrahedron Lett., 21, 4877 (1980).

    Google Scholar 

  146. P. Gesche, F. Klinger, J. Streith, and H. Strub, Tetrahedron Lett., 21, 4501 (1980).

    Google Scholar 

  147. P. N. Anderson and J. T. Sharp, J. Chem. Soc., Perkin 1, No. 6, 1331 (1980).

    Google Scholar 

  148. H. Fritz, J. M. Henlin, A. Riesen, T. Tschamber, M. Zehnder, and J. Streith, Helv. Chim. Acta, 71, 882 (1988).

    Google Scholar 

  149. V. Snieckus and J. Streith, Acc. Chem. Res., 14, 348 (1981).

    Google Scholar 

  150. J. Streith, J. R. Frost, H. Strub, and P. Goursot, Nouw. J. Chim., 4, 223 (1984).

    Google Scholar 

  151. A. Sekiguchi, Y. Kabe, and W. Ando, J. Org. Chem., 47, 2900 (1982).

    Google Scholar 

  152. M. Rahman, M. L. McKee, P. Shevlin, and S. R. Sztyrbicka, J. Am. Chem. Soc., 110, 4002 (1988).

    Google Scholar 

  153. J. T. Herron, K. J. Martinez, and R. E. Huie, Int. J. Chem. Kinet., 14, 201 (1982).

    Google Scholar 

  154. R. Jeyaraman and R. Murray, J. Am. Chem. Soc., 106, 2462 (1984).

    Google Scholar 

  155. W. Adam, Y.-Y. Chan. D. Cremer, J. Gaiss, D. Scheutrow, and M. Schidler, J. Org. Chem., 52, 2800 (1987).

    Google Scholar 

  156. H.-G. Heine, W. Hartmann, H. J. Knops, and Z. Priesnitz, Tetrahedron Lett., 24, 2635 (1983).

    Google Scholar 

  157. P. Metzner and T. N. Pham, J. Chem. Soc., Chem. Commun., No. 5, 390 (1988).

    Google Scholar 

  158. J. P. Snyder, J. Am. Chem. Soc., 96, 5005 (1974).

    Google Scholar 

  159. B. Shilling and J. P. Snyder, J. Am. Chem. Soc., 97, 4422 (1975).

    Google Scholar 

  160. O. Kikuchi, Tetrahedron Lett., 22, 859 (1981).

    Google Scholar 

  161. J. S. Splitter and M. Calvin, J. Org. Chem., 23, 65 (1958).

    Google Scholar 

  162. J. S. Splitter and M. Calvin, J. Org. Chem., 30, 3427 (1965).

    Google Scholar 

  163. N. I. Petrenko and T. N. Gerasimov, Zh. Org. Khim., 22, 231 (1986).

    Google Scholar 

  164. D. R. Boyd, P. B. Coulter, W. J. Hamilton, W. B. Jennings, and V. E. Wilson, Tetrahedron Lett., 25, 2287 (1984).

    Google Scholar 

  165. A. V. Metelitsa, O. T. Lyashik, N. V. Volbushko, I. M. Andreeva, M. I. Knyazhanskii, E. A. Medyantseva, and V. I. Minkin, Zh. Org. Khim., 22, 1446 (1986).

    Google Scholar 

  166. S. D. Isaev, E. F. Novoselov, and A. G. Yurchenko, Zh. Org. Khim., 21, 114 (1985).

    Google Scholar 

  167. N. N. Magdesieva and T. A. Sergeeva, Zh. Org. Khim., 22, 1533 (1986).

    Google Scholar 

  168. A. J. Biloski and B. Ganem, J. Org. Chem., 48, 3118 (1983).

    Google Scholar 

  169. R. D. Boyd, R. M. Campbell, P. B. Coulter, J. Grimshaw, D. C. Neill, and W. B. Jennings, J. Chem. Soc., Perkin 1, No. 4, 849 (1985).

    Google Scholar 

  170. P. J. Baldry, A. R. Forrester, M. M. Ogilvy, and R. H. Thomson, J. Chem. Soc., Perkin 1, No. 9, 2035 (1982).

    Google Scholar 

  171. E. M. Burgess, U. Zoller, and R. L. Burger, J. Am. Chem. Soc., 106, 1128 (1984).

    Google Scholar 

  172. C. S. Foote, M. L. Kacher, and C. Gu, J. Am. Chem. Soc., 103, 5949 (1981).

    Google Scholar 

  173. Y. Ogata and Y. Sawaki, J. Am. Chem. Soc., 103, 5947 (1981).

    Google Scholar 

  174. Y. Sawaki, S. Ishikawa, and H. Iwamura, J. Am. Chem. Soc., 109, 584 (1987).

    Google Scholar 

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Authors and Affiliations

  1. S. M. Kirov Ural Polytechnic Institute, 620002, Sverdlovsk

    V. A. Bakulev, V. G. Kartsev & V. S. Mokrushin

  2. Branch of Sciences of the USSR, 142432, Chernogolovka

    V. A. Bakulev, V. G. Kartsev & V. S. Mokrushin

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  1. V. A. Bakulev
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  2. V. G. Kartsev
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  3. V. S. Mokrushin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1457, November, 1989.

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Bakulev, V.A., Kartsev, V.G. & Mokrushin, V.S. Thermal and photochemical 1,3-electrocyclic reactions in the chemistry of three-membered heterocyclic compounds (review). Chem Heterocycl Compd 25, 1203–1215 (1989). https://doi.org/10.1007/BF00481513

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  • DOI: https://doi.org/10.1007/BF00481513

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