Chemistry of Heterocyclic Compounds

, Volume 5, Issue 2, pp 180–185 | Cite as

Studies in the field of 2,1,3-thia- and -selenadiazoles

LVI. Structure and reactivity of benzo-2,1,3-thia- and -selenadiazoles
  • V. G. Pesin
Article

Abstract

The results of studies on 2,1,3-thiadiazole, benzo-2,1,3-thiadiazole, benzo-2,1,3-selenadiazole, and their derivatives by chemical, physicochemical, and physical methods give no grounds for assuming that they have a quinoid structure. These results permit the statement that these heterocycles containing quatervalent sulfur or selenium are typical heteroaromatic systems satisfying Hückel's (4n+2) rule.

Keywords

Sulfur Organic Chemistry Selenium Physical Method Thiadiazole 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    V. G. Pesin and V. A. Sergeev, KhGS [Chemistry of Heterocyclic Compounds],5, 65, 1969.Google Scholar
  2. 2.
    O. Hinsberg, Ber.,22, 2889, 1889.Google Scholar
  3. 3.
    V. Luzzati, Acta cryst.,4, 193, 1951.Google Scholar
  4. 4.
    A. I. Kitaigorodskii, Organic Crystallography [in Russian], Izd-vo AN SSSR, Moscow, 1955.Google Scholar
  5. 5.
    L. S. Efros and R. M. Levit, ZhOKh,25, 199, 1955.Google Scholar
  6. 6.
    L. S. Efros and Z. V. Todres-Selektor, ZhOKh,27, 983, 1957.Google Scholar
  7. 7.
    L. S. Efros and Z. V. Todres-Selektor, ZhOKh,27, 3127, 1957.Google Scholar
  8. 8.
    L. S. Efros and A. V. El'tsov, ZhOKh,28, 2172, 1958.Google Scholar
  9. 9.
    V. L. Pozdyshev, Z. V. Todres-Selektor, and L. S. Efros, ZhOKh,30, 2551, 1960.Google Scholar
  10. 10.
    L. S. Efros, R. P. Polyakova, and M. G. Argiti, ZhOKh,32, 516, 1962.Google Scholar
  11. 11.
    L. S. Efros, Usp. khim.,29, 181, 1960.Google Scholar
  12. 12.
    V. G. Pesin, A. M. Khaletskii, and I. A. Lotsmanenko, ZhOKh,33, 1746, 1963.Google Scholar
  13. 13.
    V. G. Pesin and I. A. Belenkaya-Lotsmanenko, KhGS [Chemistry of Heterocyclic Compounds],3, 666, 1967.Google Scholar
  14. 14.
    V. G. Pesin, I. A. Belenkaya-Lotsmanenko, and A. M. Khaletskii, ZhOKh,34, 3763, 1964.Google Scholar
  15. 15.
    Chao Chih-chung, Thesis [in Russian], Leningrad Chemical and Pharmaceutical Institute, 1956.Google Scholar
  16. 16.
    L. Weinstock, Diss. Abstr.,19, 3136, 1959.Google Scholar
  17. 17.
    D. Shew, Diss. Abstr.,20, 1593, 1959.Google Scholar
  18. 18.
    V. G. Pesin, V. A. Sergeev, and A. M. Khaletskii, ZhOKh,34, 261, 1964.Google Scholar
  19. 19.
    V. G. Pesin, A. M. Khaletskii, and V. A. Sergeev, ZhOKh,32, 181, 1962.Google Scholar
  20. 20.
    N. Donaldson, The Chemistry and Technology of Ethylene Compounds [Russian translation], GKhI, Moscow, 1963.Google Scholar
  21. 21.
    E. Animal, D. Dal Monte, and E. Sandri, Boll. sci. fac. chim. ind. Bologna,22, 48, 1964.Google Scholar
  22. 22.
    I. A. Belenkaya-Lotsmanenko and V. G. Pesin, Subjects of a Scientific Conference at the Leningrad Chemical and Pharmaceutical Institue [in Russian], Leningrad, 1966.Google Scholar
  23. 23.
    M. P. Gava, R. H. Schlessinger, Tetrah. Lett.,50, 3815, 1964.Google Scholar
  24. 24.
    K. Takeda, K. Kitahonoki, M. Sugiura, V. Takano, Ber.,95, 2344, 1962.Google Scholar
  25. 25.
    S. A. D'yachenko, Thesis [in Russian], Leningrad Chemical and Pharmaceutical Institute, Leningrad, 1967.Google Scholar
  26. 26.
    I. V. Machinskaya and V. A. Barkhash, Reactions and Methods of Investigation of Organic Compounds, Vol. 9 [in Russian], GNTIKhL, Moscow, 1959.Google Scholar
  27. 27.
    A. P. Terent'ev and L. A. Yanovskaya, Reactions and Methods of Investigation of Organic Compounds, Vol. 6 [in Russian], GNTIKhL, Moscow, 1957.Google Scholar
  28. 28.
    V. S. Korobkov, I. V. Kuzin, L. A. Kaukhova, V. G. Pesin, and A. M. Khaletskii, Spectroscopy: Methods and Applications [in Russian], Nauka, Moscow, p. 130, 1964.Google Scholar
  29. 29.
    V. S. Korobkov, V. G. Pesin, L. P. Zubanova, and V. A. Sergeev, The Use of Molecular Spectroscopy in Chemistry [in Russian], Nauka, Moscow, p. 57, 1966.Google Scholar
  30. 30.
    S. G. Fridman, ZhOKh,31, 1096, 1961.Google Scholar
  31. 31.
    S. G. Fridman and L. I. Kotova, ZhOKh,32, 2871, 1962.Google Scholar
  32. 32.
    S. G. Fridman, ZhOKh,30, 1685, 1960.Google Scholar
  33. 33.
    V. G. Pesin, A. M. Khaletskii, and E. K. D'yachenko, ZhOKh,32, 3505, 1962.Google Scholar
  34. 34.
    Organic Syntheses [Russian translation], IL, Moscow,4, 426, 1953.Google Scholar
  35. 35.
    S. Gabriel and A. Sonn, Ber.,40, 4850, 1907.Google Scholar
  36. 36.
    H. C. Longuet-Higgins, Trans. Faraday Soc.,45, 173, 1949.Google Scholar
  37. 37.
    L. Pauling and V. Schomaker, J. Am. Chem. Soc.,61, 1769, 1939.Google Scholar
  38. 38.
    G. Cilento, Chem. Rev.,60, 1, 47, 1960.Google Scholar
  39. 39.
    H. Erlenmeyer and M. Leo, Helv. Chim. Acta,15, 1180, 1932;16, 733, 897, 1381, 1933.Google Scholar
  40. 40.
    G. Milazzo, Experientia,3, 370, 1947.Google Scholar
  41. 41.
    J. Godart, J. Chim. Phys.,34, 70, 1947.Google Scholar
  42. 42.
    M. R. Padhye and S. R. Desai, Trans. Faraday Soc.,49, 1386, 1953.Google Scholar
  43. 43.
    H. Erlenmeyer, E. H. Schmid, and A. Kleiber, Helv. Chim. Acta,25, 375, 1942.Google Scholar
  44. 44.
    R. Zahradnik and J. Coutecky, Coll.,26, 156, 1961.Google Scholar
  45. 45.
    R. Y. Wen, Diss. Abstr.,23, 4121, 1963.Google Scholar
  46. 46.
    F. H. Marquardt, Diss. Abstr.,21, 3272, 1961.Google Scholar
  47. 47.
    J. M. Gill, Diss. Abstr.,24, 2690, 1964.Google Scholar
  48. 48.
    R. R. McDonald, Diss. Abstr.,23, 1897, 1962.Google Scholar
  49. 49.
    F. A. Momany and R. A. Bonham, J. Am. Chem. Soc.,86, 162, 1964.Google Scholar
  50. 50.
    V. Dobyns and L. Pierce, J. Am. Chem. Soc.,85, 3553, 1963.Google Scholar
  51. 51.
    L. Pauling, Nature of the Chemical Bond and the Structure of Molecules and Crystals [Russian translation], Goskhimizdat, Moscow-Liningrad, 1947.Google Scholar
  52. 52.
    V. A. Sergeev, Thesis [in Russian], Leningrad Chemical and Pharmaceutical Institute, Leningrad, 1965.Google Scholar
  53. 53.
    E. K. D'yachenko, Thesis [in Russian], Leningrad Chemical and Pharmaceutical Institute, 1966.Google Scholar
  54. 54.
    V. G. Pesin and I. A. Belenkaya, KhGS [Chemistry of Heterocyclic Compounds],3, 289, 1967.Google Scholar
  55. 55.
    V. Sherman, Heterocyclic Compounds, Vol. 7 [Russian translation], Mir, Moscow, 1965.Google Scholar
  56. 56.
    E. R. Ward, W. H. Poesche, D. Higgins, and D. D. Heard, J. Chem. Soc., 2374, 1962.Google Scholar
  57. 57.
    R. S. Karlinskaya and N. V. Khromov-Borisov, ZhOKh,32, 1847, 1962.Google Scholar
  58. 58.
    R. W. Hill and L. E. Sutton, J. Chim. Phys.,46, 244, 1949; C. A.44, 8714, 1950.Google Scholar
  59. 59.
    O. A. Reutov, Theoretical Principles of Organic Chemistry [in Russian], MGU, 1964.Google Scholar
  60. 60.
    O. A. Osipov, V. I. Minkin, and Yu. B. Kletenik, Handbook of Dipole Moments [in Russian], Vysshaya shkola, Moscow, 1965.Google Scholar
  61. 61.
    A. I. Nunn and I. T. Ralph, J. Chem. Soc., 6769, 1965.Google Scholar
  62. 62.
    A. I. Nunn and I. T. Ralph, J. Chem. Soc., 1568, 1966.Google Scholar
  63. 63.
    W. Baker and W. D. Ollis, Quart. Rev.,11, 15, 1957.Google Scholar
  64. 64.
    V. G. Pesin, A. M. Khaletskii, Chao Chihchung, ZhOKh,27, 1575, 1957; DAN,113, 627, 1957.Google Scholar
  65. 65.
    V. G. Pesin, A. M. Khaletskii, and Chou Ch'in, ZhOKh,28, 2089, 1958; DAN, 114, 811, 1957.Google Scholar
  66. 66.
    V. G. Pesin and R. S. Muravik, Izv. AN Latv. SSR,6, 725, 1964.Google Scholar
  67. 67.
    V. G. Pesin and E. K. D'yachenko, KhGS [Chemistry of Heterocyclic Compounds],3, 97, 1967.Google Scholar
  68. 68.
    V. G. Pesin, Thesis [in Russian], LKhFI, Leningrad, 1967.Google Scholar
  69. 69.
    C. Brizzi, D. Dal Monte, and E. Sandri, Ann. Chim.,54, 476, 1964.Google Scholar
  70. 70.
    V. V. Plemenkov, Thesis [in Russian], Author's abstract, Kazan State University, 1967.Google Scholar
  71. 71.
    G. Collins, Diss. Abstr.,27 (2), 403, 1966.Google Scholar

Copyright information

© Consultants Bureau 1972

Authors and Affiliations

  • V. G. Pesin
    • 1
  1. 1.Leningrad Chemical and Pharmaceutical InstituteUSSR

Personalised recommendations