Chemistry of Heterocyclic Compounds

, Volume 8, Issue 6, pp 655–666 | Cite as

Synthesis, reactions, and properties of some selenides of the thiophene, furan, and selenophene series (review)

  • V. P. Litvinov
  • A. N. Sukiasyan
  • Ya. L. Gol'dfarb
Article

Abstract

The review is devoted to the authors' research on the synthesis and study of the reactivities of selenides of the thiophene series, and, to a lesser extent, of selenides of the furan and selenophene series. The properties of the indicated compounds — their capacity for reaction with electrophilic agents and organolithium compounds — and their spectral characteristics are examined in order to compare them with the properties of the corresponding sulfides and alkoxy derivatives.

Keywords

Sulfide Organic Chemistry Spectral Characteristic Thiophene Furan 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Ya. L. Gol'dfarb and V. P. Litvinov, Izv. Akad. Nauk SSSR, Ser. Khim., 2088 (1964).Google Scholar
  2. 2.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Izv. Akad. Nauk SSSR, Ser. Khim., 2585 (1967).Google Scholar
  3. 3.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Dokl. Akad. Nauk SSSR, 182, 340 (1968).Google Scholar
  4. 4.
    Ya. L. Gol'dfarb, V. P. Litvinov, and S. A. Ozolin', Izv. Akad. Nauk SSSR, Ser. Khim., 1419 (1968).Google Scholar
  5. 5.
    A. N. Sukiasyan, V. P. Litvinov, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., 1345 (1970).Google Scholar
  6. 6.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, Izv. Akad. Nauk SSSR, Ser. Khim., 1296 (1971).Google Scholar
  7. 7.
    V. A. Petukhov, V. P. Litvinov, A. N. Sukiasyan, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim., 1700 (1971).Google Scholar
  8. 8.
    V. S. Bogdanov, V. P. Litvinov, A. N. Sukiasyan, and Ya. L. Gol'dfarb, Zh. Organ. Khim., 7, 1257 (1971).Google Scholar
  9. 9.
    O. S. Chizhov, B. M. Zolotarev, A. N. Sukiasyan (Sukiasian), V. P. Litvinov, and Ya. L. Gol'dfarb, Org. Mass Spectr., 3, 1379 (1970).Google Scholar
  10. 10.
    Ya. L. Gol'dfarb, V. P. Litvinov, and A. N. Sukiasyan, USSR Author's Certificate No. 235,045 (1967); Byull. Izobr., No. 5, 17 (1969).Google Scholar
  11. 11.
    V. P. Litvinov, A. N. Sukiasyan, Ya. L. Gol'dfarb, and L. V. Bogacheva, Izv. Akad. Nauk SSSR, Ser. Khim., 1595 (1971).Google Scholar
  12. 12.
    V. P. Litvinov, A. N. Sukiasyan, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 466 (1972).Google Scholar
  13. 13.
    B. P. Fedorov and F. M. Stoyanovich, USSR Author's Certificate No. 165, 752 (1963); Byull. Izobr., No. 20, 20 (1964).Google Scholar
  14. 14.
    E. Niwa, H. Aoki, H. Tanaka, K. Munakata, and M. Namiki, Ber., 99, 3215 (1966).Google Scholar
  15. 15.
    H. Gilman and D. A. Shirley, J. Am. Chem. Soc., 71, 1870 (1949).Google Scholar
  16. 16.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. Obshch. Khim., 29, 2034 (1959).Google Scholar
  17. 17.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. Obshch. Khim., 29, 3631 (1959).Google Scholar
  18. 18.
    S. Gronowitz and B. Gestblom, Arkiv Kemi, 18, 513 (1962).Google Scholar
  19. 19.
    S. Gronowitz, P. Moses, A.-B. Hörnfeldt, and R. Hakansson, Arkiv Kemi, 17, 165 (1961).Google Scholar
  20. 20.
    J. Sice, J. Am. Chem. Soc., 75, 3697 (1953).Google Scholar
  21. 21.
    H. Gilman and F. J. Webb, J. Am. Chem. Soc., 71, 4062 (1949).Google Scholar
  22. 22.
    H. Gilman and R. L. Bebb, J. Am. Chem. Soc., 61, 109 (1939).Google Scholar
  23. 23.
    D. A. Shirley and K. J. Reeves, J. Organomet. Chem., 16, 1 (1969).Google Scholar
  24. 24.
    G. Wittig, U. Pockels, and H. Dröge, Ber., 17, 1903 (1938).Google Scholar
  25. 25.
    D. A. Shirley, J. R. Jonson, and J. P. Hendrix, J. Organomet. Chem., 11, 209 (1968).Google Scholar
  26. 26.
    H. Gilman and F. J. Webb, J. Am. Chem. Soc., 62, 987 (1940).Google Scholar
  27. 27.
    G. B. Bachman and L. V. Heisey, J. Am. Chem. Soc., 70, 2378 (1948).Google Scholar
  28. 28.
    S. Gronowitz, Advances in Heterocyclic Chemistry, Vol. 1, New York-London (1963), p. 1.Google Scholar
  29. 29.
    S. Gronowitz, Arkiv Kemi, 7, 361 (1954).Google Scholar
  30. 30.
    S. Gronowitz, Arkiv Kemi, 12, 239 (1958).Google Scholar
  31. 31.
    J. D. Roberts and D. Y. Curtin, J. Am. Chem. Soc., 68, 1658 (1946).Google Scholar
  32. 32.
    F. N. Jones, M. F. Zinn, and C. R. Hauser, J. Org. Chem., 28, 663 (1963).Google Scholar
  33. 33.
    B. M. Graybill and D. A. Shirley, J. Org. Chem., 31, 1221 (1966).Google Scholar
  34. 34.
    C. S. Giam and J. L. Stout, Chem. Comm., 142 (1969).Google Scholar
  35. 35.
    Z. K. Cheema, G. W. Gibson, and J. F. Eastham, J. Am. Chem. Soc., 85, 3517 (1963).Google Scholar
  36. 36.
    G. Wittig, Angew. Chem., 66, 10 (1954).Google Scholar
  37. 37.
    H. Gilman and R. V. Young, J. Am. Chem. Soc., 56, 1415 (1934).Google Scholar
  38. 38.
    R. A. Benkeser, D. J. Foster, D. M. Sauve, and J. F. Nobis, Chem. Rev., 57, 867 (1957).Google Scholar
  39. 39.
    H. D. Hartough and S. L. Meisel, Compounds with Condensed Thiophene Rings, New York (1954), p. 14.Google Scholar
  40. 40.
    Ya. L. Gol'dfarb and Ya. L. Danyushevskii, Zh. Obshch. Khim., 31, 3654 (1961).Google Scholar
  41. 41.
    A. I. Shatenshtein, A. G. Kamrad, I. O. Shapiro, Yu. I. Raneeva, and E. N. Zvyagintseva, Dokl. Akad. Nauk SSSR, 168, 364 (1966).Google Scholar
  42. 42.
    C. Price and S. Oae, Sulfur Bonding, New York (1962), p. 28.Google Scholar
  43. 43.
    H. Gilman, M. W. Van Ess, H. B. Willis, and C. G. Stuckwich, J. Am. Chem. Soc., 62, 2606 (1940).Google Scholar
  44. 44.
    H. Gilman and C. G. Stuckwich, J. Am. Chem. Soc., 67, 877 (1945).Google Scholar
  45. 45.
    S. Gronowitz, Arkiv Kemi, 13, 295 (1959).Google Scholar
  46. 46.
    V. Ramanthan and R. Levine, J. Org. Chem., 27, 1667 (1962).Google Scholar
  47. 47.
    J. Sice, J. Org. Chem., 19, 70 (1954).Google Scholar
  48. 48.
    S. Gronowitz, Arkiv Kemi, 13, 269 (1958).Google Scholar
  49. 49.
    S. Gronowitz, Arkiv Kemi, 16, 363 (1960).Google Scholar
  50. 50.
    D. A. Shirley and J. P. Hendrix, J. Organomet. Chem., 11, 217 (1968).Google Scholar
  51. 51.
    N. Gjös and S. Gronowitz, Arkiv Kemi, 30, 225 (1968).Google Scholar
  52. 52.
    S. Gronowitz and K. Halvarson, Arkiv Kemi, 8, 343 (1955).Google Scholar
  53. 53.
    A. I. Shatenshtein (Shatenstein), Tetrahedron, 18, 95 (1962).Google Scholar
  54. 54.
    H. Wynberg and A. Banties, J. Am. Chem. Soc., 82, 1447 (1960).Google Scholar
  55. 55.
    S. Gronowitz and B. Eriksson, Arkiv Kemi, 21, 335 (1963).Google Scholar
  56. 56.
    F. M. Stoyanovich and B. P. Fedorov, Zh. Organ. Khim., 1, 1282 (1965).Google Scholar
  57. 57.
    L. I. Belen'kii, N. S. Ksenzhek, and Ya. L. Gol'dfarb, Khim. Geterotsikl. Soedin., 310 (1972).Google Scholar
  58. 58.
    E. Profft, Ann., 622, 196 (1959).Google Scholar
  59. 59.
    J. Cymerman-Craig and J. W. Loder, J. Chem. Soc., 237 (1954).Google Scholar
  60. 60.
    Ya. L. Gol'dfarb, V. P. Litvinov, and V. I. Shvedov, Zh. Obshch. Khim., 30, 534 (1960).Google Scholar
  61. 61.
    B. P. Fedorov and F. M. Stoyanovich, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1834 (1960).Google Scholar
  62. 62.
    B. P. Fedorov and F. M. Stoyanovich, Zh. Obshch. Khim., 31, 238 (1961).Google Scholar
  63. 63.
    E. N. Zvyagintseva, L. I. Belen'kii, T. A. Yakushina, Ya. L. Gol'dfarb, and A. I. Shatenshtein, Zh. Obshch. Khim., 38, 2004 (1968).Google Scholar
  64. 64.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Khim. Geterotsikl. Soedin., 62 (1967).Google Scholar
  65. 65.
    Ya. L. Gol'dfarb, V. P. Litvinov, and S. A. Ozolin', Izv. Akad. Nauk SSSR, Ser. Khim., 510 (1965).Google Scholar
  66. 66.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 701 (1962).Google Scholar
  67. 67.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. Obshch. Khim., 30, 1012 (1960).Google Scholar
  68. 68.
    Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim., 1769 (1969).Google Scholar
  69. 69.
    H. Rheinboldt, in: Methoden der Organischen Chemie, Vol. 9, Stuttgart (1955), p. 1005.Google Scholar
  70. 70.
    O. K. Edwards, W. R. Gaytwaite, J. Kenyon, and H. Phillips, J. Chem. Soc., 2293 (1928).Google Scholar
  71. 71.
    E. Fromm and G. Raiziss, Ann., 374, 90 (1910).Google Scholar
  72. 72.
    K. Fries and W. Vogt, Ann., 381, 337 (1911).Google Scholar
  73. 73.
    T. Zincke and W. Frohneberg, Ber., 42, 2721 (1909).Google Scholar
  74. 74.
    T. Zincke and W. Frohneberg, Ber., 43, 837 (1910).Google Scholar
  75. 75.
    T. Zineke and R. Brune, Ber., 44, 185 (1911).Google Scholar
  76. 76.
    P. Spinoglio and M. De Gasperi, Gazz. Chim. Ital., 67, 318 (1937).Google Scholar
  77. 77.
    E. Hannig and H. Ziebandt, Pharmazie, 23, 552 (1968).Google Scholar
  78. 78.
    J. D. McCullough, J. Am. Chem. Soc., 64, 2672 (1942).Google Scholar
  79. 79.
    J. D. McCullough and B. A. Eckerson, J. Am. Chem. Soc., 67, 707 (1945).Google Scholar
  80. 80.
    J. D. McCullough and M. K. Barsh, J. Am. Chem. Soc., 71, 3029 (1949).Google Scholar
  81. 81.
    E. Bourgeois and A. Abraham, Rec. Trav. Chim., 30, 407 (1911).Google Scholar
  82. 82.
    F. Krafft and W. Vorster, Ber., 26, 2819 (1893).Google Scholar
  83. 83.
    Ya. L. Danyushevskii, M. A. Marakatkina, and Ya. L. Gol'dfarb, Zh. Organ. Khim., 4, 474 (1968).Google Scholar
  84. 84.
    A. Bugge, Acta Chem. Scand., 23, 1823 (1969).Google Scholar
  85. 85.
    V. P. Litvinov and G. Frenkl, Izv. Akad. Nauk SSSR, Ser. Khim., 1328 (1968).Google Scholar

Copyright information

© Consultants Bureau 1974

Authors and Affiliations

  • V. P. Litvinov
    • 1
  • A. N. Sukiasyan
    • 1
  • Ya. L. Gol'dfarb
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations