Skip to main content
Log in

Redox transformations of compounds of the thiophene series (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Chemical and electrochemical methods for the reduction and oxidation of compounds of the thiophene series that consist in transformations of the substituents or the heteroring and are suitable for preparative use are described.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. L. I. Belen'kii, E. P. Zakharov, M. A. Kalik, V. P. Litvinov, F. M. Stoyanovich, S. Z. Taits, and B. P. Fabrichnyi, New Directions in the Chemistry of Thiophene [in Russian], Ya. L. Gol'dfarb, ed., Nauka, Moscow (1976).

    Google Scholar 

  2. K. A. Bilevich and O. Yu. Okhlobystin, Usp. Khim., 37, 2162 (1968).

    Google Scholar 

  3. M. Baizer (editor), The Electrochemistry of Organic Compounds [Russian translation], Mir, Moscow (1976).

    Google Scholar 

  4. A. P. Tomilov, M. Ya. Fioshin, and V. A. Smirnov, The Electrochemical Synthesis of Organic Substances [in Russian], Khimiya, Moscow (1976).

    Google Scholar 

  5. Ya. P. Stradyn', in: Advances in the Chemistry of Furan [in Russian], É. Ya. Lukevits, ed., Zinatne, Riga (1977), p. 66.

    Google Scholar 

  6. V. G. Mairanovskii, Zh. Vses. Khim. Ova., 22, 334 (1977).

    Google Scholar 

  7. A. Khodair, A. Swelim, and F. El Sheiku, Int. J. Sulfur Chem., B6, 195 (1971).

    Google Scholar 

  8. A. Swelim, A. Khodair, and F. El Sheiku, Int. J. Sulfur Chem., B6, 213 (1971).

    Google Scholar 

  9. D. N. Kursanov, Z. N. Parnes, N. M. Loim, and M. I. Kalinkin, Ionic Hydrogenation [in Russian], Khimiya, Moscow (1979).

    Google Scholar 

  10. D. W. H. MacDowell and A. W. Springsteen, J. Org. Chem., 41, 3046 (1976).

    Google Scholar 

  11. H. A. Michel, G. Mousset, J. Simonet, and H. Lund, Electrochim. Acta, 20, 143 (1975).

    Google Scholar 

  12. Ya. L. Gol'dfarb, S. Z. Taits, and V. N. Bulgakova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1299 (1963).

    Google Scholar 

  13. W. J. King and F. F. Nord, J. Org. Chem., 14, 638 (1949).

    Google Scholar 

  14. L. I. Belen'kii, S. Z. Taits, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR. Otdel. Khim. Nauk, No. 9, 1706 (1961).

    Google Scholar 

  15. M. A. Ryashentseva, O. A. Kalinovskii, Kh. M. Minachev, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 6, 694 (1966).

    Google Scholar 

  16. M. A. Ryashentseva, Kh. M. Minachev, E. P. Belanova, B. P. Fabrichnyi, and Yu. B. Vol'kenshtein, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2152 (1977).

    Google Scholar 

  17. M. R. Kegelman and E. V. Brown, J. Am. Chem. Soc., 75, 5961 (1953).

    Google Scholar 

  18. C. Buehler and D. E. Pearson, Survey of Organic Syntheses, Wiley (1970).

  19. T. Mizutani, Y. Ume, and T. Matsuo, Japanese Patent No. 135932; Chem. Abstr., 82, 155744 (1975).

    Google Scholar 

  20. T. Mizutani, Y. Ume, and T. Matsuo, Japanese Patent No. 135933; Chem. Abstr., 82, 155745 (1975).

    Google Scholar 

  21. F. W. Dunn and K. Dittmer, J. Am. Chem. Soc., 68, 2561 (1946).

    Google Scholar 

  22. E. Laviron and J. Tirouflet, Adv. Polarogr., 2, 727 (1960).

    Google Scholar 

  23. S. G. Mairanovskii, N. V. Barashkova, and Yu. B. Vol'kenshtein, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1539 (1965).

    Google Scholar 

  24. C. Caullet, M. Salaün, and H. Hebert, Compt. Rend., C264, 228 (1967).

    Google Scholar 

  25. P. Foulatier and C. Caullet, Compt. Rend., C279, 25 (1974).

    Google Scholar 

  26. L. I. Vykhodtseva and L. N. Nekrasov, Élektrokhimiya. 13, 1239 (1977).

    Google Scholar 

  27. L. I. Vykhodtseva and L. N. Nekrasov, Élektrokhimiya, 15, 741 (1979).

    Google Scholar 

  28. V. P. Gultyai, S. G. Mairanovskii, T. Ya. Rubinskaya, I. V. Proskurovskaya, and N. P. Rodionov, Élektrokhimiya, 15, 851 (1979).

    Google Scholar 

  29. V. P. Gul'tyai and A. M. Moiseenkov, Zh. Org. Khim., 16, 1026 (1980).

    Google Scholar 

  30. E. V. Kryukova and A. P. Tomilov, Élektrokhimiya, 5, 869 (1969).

    Google Scholar 

  31. J. H. Stocker and R. H. Jenevein, Collect. Czech. Chem. Commun., 36, 925 (1971).

    Google Scholar 

  32. P. Foulatier, J.-P. Salaün, and C. C. Caullet, Compt. Rend,m C279, 779 (1974).

    Google Scholar 

  33. S. Z. Taits, F. D. Alashev, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 402 (1969).

    Google Scholar 

  34. L. I. Belen'kii, I. B. Karmanova, Yu. B. Vol'kenshtein, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 956 (1971).

    Google Scholar 

  35. J. Srogl, M. Janda, I. Stibor, and H. Prochazka, Z. Chem., 11, 421 (1971).

    Google Scholar 

  36. R. A. Benkeser and J. M. Gaul, J. Am. Chem. Soc., 92, 720 (1970).

    Google Scholar 

  37. R. A. Benkeser, H. M. Foley, and J. M. Gaul, J. Am. Chem. Soc., 92, 3232 (1970).

    Google Scholar 

  38. V. S. Mikhailov, S. G. Mairanovskii, and V. P. Gul'tyai, Électrokhimiya, 7, 1206 (1971).

    Google Scholar 

  39. J. Nahaya, H. Kinoshita, and S. Ono, J. Chem. Soc. Jpn., Pure Chem. Sect., 78, 935 (1957).

    Google Scholar 

  40. S. Gronowitz, Acta Chem. Scand., 13, 1045 (1959).

    Google Scholar 

  41. S.-O. Lawesson, Ark. Kem., 11, 317 (1957).

    Google Scholar 

  42. I. O. Shapiro, L. I. Belen'kii, I. A. Romanskii, F. M. Stoyanovich, Ya. L. Gol'dfarb, and A. I. Shatenshtein, Zh. Obshch. Khim., 38, 1998 (1968).

    Google Scholar 

  43. B. P. Fabrichnyi, I. F. Shalavina, and Ya. L. Gol'dfarb, USSR Inventor's Certificate No. 170521; Byul. Izobret., No. 9, 26 (1965).

  44. B. P. Fabrichnyi, I. F. Shalavina, Ya. L. Gol'dfarb, Dokl. Akad. Nauk SSSR, 162, 120 (1965).

    Google Scholar 

  45. B. P. Fabrichnyi, I. F. Shalavina, S. M. Kostrova, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., No. 10, 1358 (1971).

    Google Scholar 

  46. R. Mozingo, S. A. Harris, D. E. Wolf, C. E. Hoffhine, W. R. Easton, and K. Folkers, J. Am. Chem. Soc., 67, 2092 (1945).

    Google Scholar 

  47. J. C. Barker, J. F. C. Coutts, and P. R. Huddleston, Chem. Commun., No. 10, 615 (1972).

    Google Scholar 

  48. J. F. Bunnett, and R. R. Victor, J. Am. Chem. Soc., 90, 810 (1968).

    Google Scholar 

  49. F. M. Stoyanovich, G. I. Gorushkina, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 387 (1968).

    Google Scholar 

  50. Z. V. Todres, F. M. Stoyanovich, Ya. L. Gol'dfarb, and D. N. Kursanov, Khim. Geterotsikl. Soedin., No. 5, 632 (1973).

    Google Scholar 

  51. Ya. L. Gol'dfarb, G. P. Pokhil, and L. I. Belen'kii, Dokl. Akad. Nauk SSSR, 167, 823 (1966).

    Google Scholar 

  52. B. P. Fedorov, G. I. Gorushkina, and Ya. L. Gol'dbarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2049 (1967).

    Google Scholar 

  53. M. A. Ryashentseva, O. A. Kalinovskii, Kh. M. Minachev, Ya. L. Gol'dfarb, Zh. Org. Khim., 1, 1004 (1965).

    Google Scholar 

  54. W. Steinkopf, Ann. Chem., 403, 17 (1914).

    Google Scholar 

  55. D. L. Eck and G. W. Stacy, J. Heterocycl. Chem., 6, 147 (1969).

    Google Scholar 

  56. S. G. Mairanovskii, N. V. Barashkova, and Yu. B. Vol'kenshtein, Éleketrokhimiya, 1, 72 (1965).

    Google Scholar 

  57. É. S. Levin and Z. N. Fodiman, Zh. Fiz. Khim., 28, 601 (1954).

    Google Scholar 

  58. M. Person, R. Guilard, and P. Fournari, Compt. Rend., C264, 1727 (1967).

    Google Scholar 

  59. S. G. Mairanovskii and A. D. Filonova, Elektrokhimiya, 1, 1044 (1965).

    Google Scholar 

  60. V. S. Mikhailov, V. P. Gul'tyai, and S. G. Mairanovskii, Élektrokhimiya, 8, 138 (1972).

    Google Scholar 

  61. F. M. Halla, J. Pinson, and J. M. Saveant, J. Electroanal. Chem., 89, 347 (1978).

    Google Scholar 

  62. W. van Tilborg and C. J. Smit, Tetrahedron Lett., No. 41, 3651 (1977).

    Google Scholar 

  63. F. M. Stoyanovich, S. G. Mairanovskii, Ya. L. Gol'dfarb, and I. A. D'yachenko, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1439 (1971).

    Google Scholar 

  64. Ya. P. Stradyn', A. Yurashek, and G. Raikhmanis, Zh. Obshch. Khim., 35, 768 (1965).

    Google Scholar 

  65. J. Tirouflet and J.-P. Chane, Compt. Rend., 253, 500 (1956).

    Google Scholar 

  66. J. Tirouflet and P. Fournari, Compt. Rend., 246, 2003 (1958).

    Google Scholar 

  67. L. I. Belen'kii, É. I. Novikova, I. A. D'yachenko, and Ya. L. Gol'dfarb, Zh. Org. Khim., 7, 1736 (1971).

    Google Scholar 

  68. P. Zuman, Substitution Effects in Organic Polarography, Plenum Press, New York (1967).

    Google Scholar 

  69. P. N. Confalone, G. Pizzoloto, and M. R. Uskokovic, J. Org. Khim., 42, 135 (1966).

    Google Scholar 

  70. H. Broadbent, L. H. Staush, and N. L. Jarvis, J. Am. Chem. Soc., 76, 1516 (1954).

    Google Scholar 

  71. M. A. Ryashentseva and Kh. M. Minachev, Usp. Khim., 38, 2050 (1969).

    Google Scholar 

  72. G. B. Hatch, U.S. Patent No. 2648675; Chem. Abstr., 48, 8264 (1954).

    Google Scholar 

  73. D. N. Kursanov, Z. N. Parnes, G. N. Bolestova, and L. I. Belen'kii, USSR Inventor's Certificate No. 408950; Byull. Izobret., No. 48, 68 (1973).

  74. D. N. Kursanov, Z. N. Parnes, G. I. Bolestova, and L. I. Belen'kii, Tetrahedron, 31, 311 (1975).

    Google Scholar 

  75. Z. N. Parnes, G. I. Bolestova, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 478 (1976).

    Google Scholar 

  76. Z. N. Parnes, Yu. I. Lyakhovetskii, S. N. Dolgova, A. S. Pakhomov, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2526 (1977).

    Google Scholar 

  77. Z. N. Parnes, Yu. I. Lyakhovetskii, M. I. Kalinkin, L. I. Belen'kii, and D. N. Kursanov, Tetrahedron, 34, 1703 (1978).

    Google Scholar 

  78. J. Wrister, J. Am. Chem. Soc., 5051 (1977).

  79. S. F. Birch and D. T. McAllan, J. Chem. Soc., No. 10, 2556 (1951).

    Google Scholar 

  80. S. G. Mairanovskii, L. I. Kosychenko, and S. Z. Taits, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1382 (1980).

    Google Scholar 

  81. H. Lund, M.-A. Michel, and L. Simonet, Acta Chem. Scand., B28, 900 (1974).

    Google Scholar 

  82. S. G. Mairanovskii, L. I. Kosychenko, and S. Z. Taits, Élektrokhimiya, 13, 1250 (1977).

    Google Scholar 

  83. P. Cavalieri d'Oro, A. Mangini, G. F. Pedulli, P. Spangnolo, and M. Tiecco, Tetrahedron Lett., No. 48, 4179 (1969).

    Google Scholar 

  84. V. Galassó and N. Trinajstic, J. Chim. Phys. Phys. Chim. Biol., 70, 1489 (1973).

    Google Scholar 

  85. J. M. McIntosh and H. B. Goodbrand, Tetrahedron Lett., No. 34, 3157 (1973).

    Google Scholar 

  86. R. M. Kellogg, S. Wassenaar, and J. Buter, Tetrahedron Lett., No. 54, 4689 (1970).

    Google Scholar 

  87. J. M. McIntosh and R. S. Steevensz, Can. J. Chem., 52, 1934 (1974).

    Google Scholar 

  88. V. P. Gul'tyai, I. V. Proskurovskaya, T. Ya. Rubinskaya, A. V. Lozanova, A. M. Moiseenkov, and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1576 (1979).

    Google Scholar 

  89. R. M. Kellogg, J. Am. Chem. Soc., 93, 2344 (1971).

    Google Scholar 

  90. B. D. Tilak, H. S. Desai, and S. S. Gupta, Tetrahedron Lett., No. 24, 1609 (1964).

    Google Scholar 

  91. G. I. Bolestova, E. P. Zakharov, S. P. Dolgova, Z. N. Parnes, and D. N. Kursanov, Khim. Geterotsikl. Soedin., No. 9, 1206 (1975).

    Google Scholar 

  92. N. I. Putokhin and V. S. Egorova, Zh. Obshch. Khim., 18, 1866 (1948).

    Google Scholar 

  93. Ya. L. Gol'dfarb, A. V. Semenovskii, E. P. Zakharov, G. V. Davydova, and F. M. Stoyanovich, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 480 (1979).

    Google Scholar 

  94. I. A. Avrutskaya and G. A. Kokarev, Electrosynthesis and Bioelectrochemistry. Progress in the Electrochemistry of Organic Compounds [in Russian], Nauka, Moscow (1975), p. 34.

    Google Scholar 

  95. V. S. Mikhailov, V. P. Gul'tyai, S. G. Mairanovskii, S. Z. Taits, and I. V. Proskurovskaya, Elektrokhimiya, 11, 888 (1975).

    Google Scholar 

  96. Ya. L. Gol'dfarb and E. P. Zakharov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1909 (1975).

    Google Scholar 

  97. Ya. L. Gol'dfarb and E. P. Zakharov, Khim. Geterotsikl. Soedin., No. 3, 377 (1977).

    Google Scholar 

  98. E. P. Zakharov and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., No. 8, 1877 (1978).

    Google Scholar 

  99. Ya. L. Gol'dfarb and E. P. Zakharov, Khim. Geterotsikl. Soedin., No. 12, 1633 (1971).

    Google Scholar 

  100. Ya. L. Gol'dfarb and E. P. Zakharov, Zh. Org. Khim., 6, 1757 (1970).

    Google Scholar 

  101. Ya. L. Gol'dfarb and E. P. Zakharov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2160 (1973).

    Google Scholar 

  102. Ya. L. Gol'dfarb and E. P. Zakharov, Khim. Geterotsikl. Soedin., No. 11, 1499 (1975).

    Google Scholar 

  103. Ya. L. Gol'dfarb, E. P. Zakharov, A. S. Shashkov, and F. M. Stoyanovich, Zh. Org. Khim., 16, 1523 (1980).

    Google Scholar 

  104. Ya. L. Gol'dfarb, B. P. Fabrichnyi, and I. F. Shalavina, Tetrahedron, 18, 21 (1962).

    Google Scholar 

  105. Ya. L. Gol'dfarb, S. Z. Taits, and L. I. Belen'kii, Tetrahedron, 19, 1851 (1963).

    Google Scholar 

  106. V. S. Mikhailov, Master's Dissertation, Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow (1972).

    Google Scholar 

  107. J. Joule and G. Smith, Heterocyclic Chemistry, Van Nostrand Reinhold (1972).

  108. C. N. Skold and R. H. Schlessinger, Tetrahedron Lett., No. 10, 791 (1970).

    Google Scholar 

  109. W. van Tilborg, Rev. Trav. Chim., 95, 140 (1976).

    Google Scholar 

  110. L. Frierman, D. H. Fisher, and H. Shechter, J. Org. Chem., 30, 1453 (1965).

    Google Scholar 

  111. P. A. Konstantinov, T. V. Shchedrinskaya, I. V. Zakharov, and M. N. Volkov, Zh. Org. Khim., 8, 2590 (1972).

    Google Scholar 

  112. P. A. Konstantinov, T. V. Shchedrinskaya, and I. V. Zakharov, USSR Inventor's Certificate No. 335248; Ref. Zh. Khim., 6N220 (1973).

  113. T. V. Shchedrinskaya, P. A. Konstantinov, V. P. Litvinov, É. G. Ostapenko, I. V. Zakharov, and M. N. Volkov, Zh. Obshch. Khim., 44, 837 (1974).

    Google Scholar 

  114. M. N. Volkov, O. A. Kazakova, É. G. Ostapenko, P. A. Konstantinov, and R. I. Shunik, Zh. Org. Khim., 15, 1199 (1979).

    Google Scholar 

  115. T. V. Shchedrinskaya, P. A. Konstantinov, and M. N. Volkov, Khim. Geterotsikl. Soedin., No. 1, 57 (1977).

    Google Scholar 

  116. M. I. Usanovich, A. V. Solomin, and E. I., Kryuchkova, Élektrokhimiya, 6, 894 (1970).

    Google Scholar 

  117. R. Clarke, A. Kuhn, and E. Okah, Chem. Br., 11, 59 (1975).

    Google Scholar 

  118. L. V. Timokhina, A. S. Nakhmanovich, and T. P. Shcherbina, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2851 (1974).

    Google Scholar 

  119. Z. Horii, K. Sakurai, K. Tomino, and T. Homishi, J. Pharm. Soc. Jpn., 76, 1101 (1956).

    Google Scholar 

  120. W. J. Raich and C. S. Hamilton, J. Am. Chem. Soc., 79, 3800 (1957).

    Google Scholar 

  121. H. R. Snyder, L. A. Caprino, J. F. Zack, and J. F. Mills, J. Am. Chem. Soc., 79, 2556 (1957).

    Google Scholar 

  122. M. Fetizon, F. Gomez-Parra, and J.-M. Louis, J. Heterocycl. Chem., 13, 525 (1976).

    Google Scholar 

  123. H. Lund, Acta Chem. Scand., 11, 491 (1957).

    Google Scholar 

  124. M. Janda, J. Srogl, and M. Synackova, Collect. Czech. Chem. Commun., 37, 2584 (1972).

    Google Scholar 

  125. M. Janda, J. Srogl, M. Nemec, and I. Stibor, International Symposium on Low-Molecular-Weight Sulfur-Containing Natural Products, Poland (1976).

  126. K. Yoshida and T. Fueno, J. Org. Chem., 36, 1523 (1971).

    Google Scholar 

  127. H. Tanaka, Y. Kobayasi, and S. Torii, J. Org. Chem., 41, 3482 (1976).

    Google Scholar 

  128. J. Srogl, M. Janda, and I. Stibor, Collect. Czech. Chem. Commun., 39, 185 (1974).

    Google Scholar 

  129. M. Janda and L. Paviensky, Collect. Czech. Chem. Commun., 32, 2675 (1967).

    Google Scholar 

  130. M. Nemec, M. Janda, J. Srogl, and I. Stibor, Collect. Czech. Chem. Commun., 39, 3527 (1974).

    Google Scholar 

  131. A. P. Yakubov, L. I. Belen'kii, and Ya. L. Gol'dfarb, Zh. Org. Khim., 7, 525 (1971).

    Google Scholar 

  132. A. Peter, Chem. Ber., 18, 537 (1885).

    Google Scholar 

  133. M. G. Johnson, J. P. Turnbull, and H. A. Crige, West German Patent Application No. 2528786 (1976); Chem. Abstr., 84, 150492 (1976).

    Google Scholar 

  134. O. Manousek and J. Volke, J. Electroanal. Chem., 43, 365 (1973).

    Google Scholar 

  135. W. Boardman and G. Edwards, J. Electroanal. Chem., 33, 95 (1971).

    Google Scholar 

  136. L. A. Mirkind, M. Ya. Fioshin, and L. V. Aniskova, Dokl. Akad. Nauk SSSR, 219, 1127 (1974).

    Google Scholar 

  137. P. A. Konstantinov, I. V. Shelepin, and P. M. Kolesnikova, Khim. Geterotsikl. Soedin., No. 7, 915 (1971).

    Google Scholar 

  138. Ya. L. Gol'dfarb and M. S. Kondakova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, No. 6, 1131 (1952).

    Google Scholar 

  139. Ya. L. Gol'dfarb and I. S. Korsakova, Dokl. Akad. Nauk SSSR, 89, 301 (1953).

    Google Scholar 

  140. Ya. L. Gol'dfarb and M. L. Kirmalova, Dokl. Akad. Nauk SSSR, 91, 539 (1953).

    Google Scholar 

  141. J. L. Melles and H. J. Baker, Rec. Trav. Chim., 72, 314 (1953).

    Google Scholar 

  142. J. L. Melles, Rec. Trav. Chim., 71, 869 (1952).

    Google Scholar 

  143. W. L. Mock, J. Am. Chem. Soc., 92, 7610 (1970).

    Google Scholar 

  144. K. Torssell, Acta Chem. Scand., B30, 353 (1976).

    Google Scholar 

  145. K. Yoshida, T. Saeki, and T. Fueno, J. Org. Chem., 36, 3673 (1971).

    Google Scholar 

  146. N. L. Weinberg and H. R. Weinberg, Chem. Rev., 68, 449 (1968).

    Google Scholar 

  147. I. Stibor, J. Srogl, and M. Janda, Chem. Commun., No. 10, 397 (1975).

    Google Scholar 

  148. S. Torii, H. Tanaka, T. Anoda, and Y. Simizu, Chem. Lett., No. 5, 495 (1976).

    Google Scholar 

  149. M. Janda, Collect. Czech. Chem. Commun., 28, 2524 (1963).

    Google Scholar 

  150. J. Srogl, M. Janda, and M. Valentova, Collect. Czech. Chem. Commun., 35, 148 (1970).

    Google Scholar 

  151. N. Clauson-Kaas, F. Limborg, and K. Gleus, Acta Chem. Scand., 6, 531 (1952).

    Google Scholar 

  152. N. N. Nechiporenko, Zh. Prikl. Khim., 29, 1337 (1956).

    Google Scholar 

  153. M. Janda, J. Srogl, M. Nemec, and A. Janosova, Collect. Czech. Chem. Commun., 38, 1221 (1973).

    Google Scholar 

  154. M. Janda, J. Srogl, and M. Nemec, Czechoslovakian Patent No. 155895; Chem. Abstr., 83, 27613 (1975).

    Google Scholar 

  155. O. Yu. Okhlobystin, Electron Transfer in Organic Reactions [in Russian], Izd. Rostovsk. Gos. Univ. (1974).

  156. Z. V. Todres, Usp. Khim., 47, 260 (1978).

    Google Scholar 

  157. L. A. Blyumenfel'd, L. V. Bryukhovetskaya, G. V. Fomin, and S. M. Shein, Zh. Fiz. Khim., 44, 931 (1970).

    Google Scholar 

  158. L. I. Belen'kii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 344 (1975).

    Google Scholar 

  159. J. H. Hoggett, R. B. Moodie, and K. Shofield, J. Chem. Soc., B, No. 1, 1 (1969).

    Google Scholar 

  160. J. H. Ridd, Acc. Chem. Res., 4, 248 (1971).

    Google Scholar 

  161. B. Ostman, Ark. Kem., 19, 499 (1962).

    Google Scholar 

  162. C. L. Perrin, J. Am. Chem. Soc., 99, 5576 (1977).

    Google Scholar 

  163. M. R. Draper and J. H. Ridd, Chem. Commun., No. 10, 445 (1978).

    Google Scholar 

  164. L. Eberson, L. Jonsson, and F. Radner, Acta Chem. Scand., B32, 749 (1978).

    Google Scholar 

  165. I. P. Beletskaya and A. N. Kashin, Zh. Vses. Khim. Ova., 24, 148 (1979).

    Google Scholar 

  166. M. Nemec, M. Janda, and J. Srogl, Collect. Czech. Chem. Soc., 38, 3857 (1973).

    Google Scholar 

  167. T. Abe, S. Nagase, and H. Baba, Bull. Chem. Soc., Jpn., 46, 3845 (1973).

    Google Scholar 

  168. M. Libert and C. Caullet, Compt. Rend., C278, 439 (1974).

    Google Scholar 

  169. J. K. Kim and J. F. Bunnett, J. Am. Chem. Soc., 92, 7463 (1970).

    Google Scholar 

  170. I. P. Beletskaya and V. N. Drozd, Usp. Khim., 48, 793 (1979).

    Google Scholar 

  171. J. F. Bunnett and B. F. Gloor, Heterocycles, 5, 377 (1976).

    Google Scholar 

  172. Ya. L. Gol'dfarb, A. P. Yakubov, and L. I. Belen'kii, Khim. Geterotsikl. Soedin., No. 8, 1044 (1979).

    Google Scholar 

  173. J. Pinson and J.-M. Saveant, J. Am. Chem. Soc., 100, 1055 (1978).

    Google Scholar 

  174. S. Wawzonek and A. J. Gunderson, J. Electrochem. Soc., 111, 324 (1964).

    Google Scholar 

  175. J. Simonet, M. A. Michel, and H. Lund, Acta Chem. Scand., B29, 489 (1975).

    Google Scholar 

  176. L. H. Kristensen and H. Lund, Acta Chem. Scand., 33, 735 (1979).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–743, June, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Belen'kii, L.I., Gul'tyai, V.P. Redox transformations of compounds of the thiophene series (review). Chem Heterocycl Compd 17, 523–541 (1981). https://doi.org/10.1007/BF00503474

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00503474

Keywords

Navigation