Skip to main content
SpringerLink
Log in

Thiapyrylium salts (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The literature data touching upon the synthesis of thiapyrylium salts and the stability of the thiapyrylium cation as compared with its isoelectronic analogs, as well as the nucleophilic, oxidation, anion-exchange, and other reactions of the salts with substituted and unsubstituted thiapyrylium cations are examined in this review.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. J. Degani and R. Fochi, Gazz. Chim. Ital., 97, 397 (1967).

    Google Scholar 

  2. A. Lütringhaus and N. Engelhard, Angew. Chem., 73, 218 (1961).

    Google Scholar 

  3. J. Kontecky, Coll. Czech. Chem. Commun., 24, 1607 (1959).

    Google Scholar 

  4. J. Zahradnik and J. Kontecky, Coll. Czech. Chem. Commun., 28, 1117 (1963).

    Google Scholar 

  5. J. Degani, R. Fochi, and C. Vincenzi, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 21 (1965).

    Google Scholar 

  6. G. Suld and C. Price, J. Amer. Chem. Soc., 54, 2094 (1962).

    Google Scholar 

  7. C. Price, M. Hori, and P. M. Polk, J. Amer. Chem. Soc., 85, 2278 (1963).

    Google Scholar 

  8. M. Polk, M. Siskin, and C. Price, J. Amer. Chem. Soc., 91, 1206 (1969).

    Google Scholar 

  9. C. Price and D. H. Follweiler, J. Org. Chem., 34, 3202 (1969).

    Google Scholar 

  10. C. Price, T. Parasaran, and T. V. Laksiminarayan, J. Amer. Chem. Soc., 88, 1034 (1966).

    Google Scholar 

  11. C. Price and H. Pirelahi, J. Org. Chem., 37, 1718 (1972).

    Google Scholar 

  12. C. Price, M. Siskin, and C. Miao, J. Org. Chem., 37, 794 (1972).

    Google Scholar 

  13. R. Wizinger and P. Ulrich, Helv. Chim. Acta, 39, 207 (1956).

    Google Scholar 

  14. R. Wizinger and P. Ulrich, Helv. Chim. Acta, 39, 217 (1956).

    Google Scholar 

  15. K. Kasyesy, J. Masacugu, K. Hicao, and F. Kanyity, J. Chem. Soc. Japan, Pure Chem. Soc., 84, 432 (1963).

    Google Scholar 

  16. G. Suld and C. Price, J. Amer. Chem. Soc., 83, 1770 (1961).

    Google Scholar 

  17. G. Suld and C. Price, J. Amer. Chem. Soc., 84, 2090 (1962).

    Google Scholar 

  18. K. Dimroth, K. Wolf, and H. Kroke, Ann., 678, 183 (1964).

    Google Scholar 

  19. K. Dimroth, H. Kroke, and K. Wolf, Ann., 678, 202 (1964).

    Google Scholar 

  20. R. Wizinger and H. Angeliner, H. Angeliner, Helv. Chim. Acta, 49, 2046 (1966).

    Google Scholar 

  21. R. Pettit, Tetrahedron Lett., 11 (1960).

  22. Z. S. Ariyan and H. Suschitzky, J. Chem. Soc., 2242 (1961).

  23. W. Dilthey, J. prakt. Chem., 131, 1 (1931).

    Google Scholar 

  24. W. Dilthey and E. Floret, Ann., 440, 89 (1924).

    Google Scholar 

  25. C. D. Nenitzescu and C. N. Jonescu, Ann., 491, 189 (1931).

    Google Scholar 

  26. G. N. Dorofeenko and S. M. Luk'yanov, Khim. Geterotsikl. Soedin., 886 (1972).

  27. A. T. Balaban, Compt. Rend., 256, 4239 (1963).

    Google Scholar 

  28. J. A. Allan and G. A. Reynold, J. Org. Chem., 33, 1102 (1968).

    Google Scholar 

  29. M. Siemiatycki and R. Fugnitto, Bull. Soc. Chim. France, 538 (1961).

  30. M. Simalty and J. Jarretto, Bull. Soc. Chim. France, 2959 (1966).

  31. G. N. Dorofeenko, S. V. Krivun, and V. V. Mezheretskii, Zh. Obshch. Khim., 35, 632 (1965).

    Google Scholar 

  32. G. N. Dorofeenko, G. A. Korol'chenko, and S. V. Krivun, Khim. Geterotsikl. Soedin, 817 (1965).

  33. A. T. Balaban and N. S. Barbulescu, Rev. Roum. Chim., 11, 109 (1966).

    Google Scholar 

  34. J. Degani, R. Fochi, and C. Vincenzi, Gazz. Chim. Ital., 94, 451 (1964).

    Google Scholar 

  35. J. Degani and C. Vincenzi, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 245 (1965).

    Google Scholar 

  36. J. Degani, R. Fochi, and C. Vincenzi, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 241 (1965).

    Google Scholar 

  37. J. Degani, R. Fochi, and C. Vincenzi, Tetrahedron Lett., 1167 (1963).

  38. E. Molenaar and J. Strating, Tetrahedron Lett., 2941 (1965).

  39. B. D. Tilak and V. M. Vaidya, Tetrahedron Lett., 489 (1963).

  40. B. D. Tilak, R. B. Mitrac, and C. V. Deshpande, Tetrahedron Lett., 3569 (1965).

  41. V. G. Kharchenko, S. K. Klimenko, A. M. Plaksina, and A. B. Yakoreva, Zh. Organ. Khim., 2, 1122 (1966).

    Google Scholar 

  42. V. G. Kharchenko, V. I. Kleimenova, N. M. Kupranets, N. V. Polikarpova, and A. R. Yakoreva, Zh. Organ. Khim., 4, 2054 (1968).

    Google Scholar 

  43. V. G. Kharchenko, S. K. Klimenko, V. I. Kleimenova, and N. M. Kupranets, Zh. Organ. Khim., 5, 1711 (1969).

    Google Scholar 

  44. V. G. Kharchenko, N. M. Kupranets, V. I. Kleimenova, A. A. Rassudova, M. E. Stankevich, N. M. Yartseva, and A. R. Yakoreva, Zh. Organ. Khim., 6, 1119 (1970).

    Google Scholar 

  45. V. G. Kharchenko, M. E. Stankevich, A. R. Yakoreva, and E. G. Lelienfel'd, Khim. Geterotsikl. Soedin., 422 (1971).

  46. V. G. Kharchenko, M. E. Stankevich, A. R. Yakoreva, A. A. Rassudova, and N. M. Yartseva, Khim. Geterotsikl. Soedin., 916 (1972).

  47. V. G. Kharchenko, M. E. Stankevich, N. M. Kupranets, A. R. Yakoreva, V. I. Kleimenova, and S. K. Klimenko, Zh. Organ. Khim., 8, 193 (1972).

    Google Scholar 

  48. V. G. Kharchenko, N. M. Yartseva, and A. A. Rassudova, Zh. Organ. Khim., 6, 1513 (1970).

    Google Scholar 

  49. V. G. Kharchenko, S. K. Klimenko, and T. I. Krupina, Zh. Organ. Khim., 3, 1344 (1967).

    Google Scholar 

  50. V. G. Kharchenko, S. K. Klimenko, and T. I. Krupina, Khim. Geterotsikl. Soedin., No. 3, 76 (1971).

    Google Scholar 

  51. V. G. Kharchenko, S. K. Klimenko, V. I. Kleimenova, N. M. Kupranets, and A. R. Yakoreva, Khim. Geterotsikl. Soedin., No. 3, 73 (1971).

    Google Scholar 

  52. V. G. Kharchenko, V. I. Kleimenova, and A. R. Yakoreva, Khim. Geterotsikl. Soedin., No. 3, 79 (1971).

    Google Scholar 

  53. V. G. Kharchenko and V. I. Kleimenova, Zh. Organ. Khim., 7, 613 (1971).

    Google Scholar 

  54. J. Faust, Z. Chem., 8, 171 (1968).

    Google Scholar 

  55. B. Föhlisch and D. Krakenberger, Ber., 101, 3990 (1968).

    Google Scholar 

  56. D. M. Kinnon, Can. J. Chem., 48, 3388 (1970).

    Google Scholar 

  57. H. Hartmann, J. prakt. Chem., 313, 1113 (1971).

    Google Scholar 

  58. J. Degani, R. Fochi, and G. Spunta, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 243 (1965).

    Google Scholar 

  59. R. G. Tarubo, D. L. Sullivan, and R. Pettit, J. Amer. Chem. Soc., 86, 5630 (1964).

    Google Scholar 

  60. J. Degani and R. Fochi, Gazz. Chim. Ital., 97, 397 (1967).

    Google Scholar 

  61. J. Degani and C. Vincenzi, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 249 (1965).

    Google Scholar 

  62. G. Canalini, J. Degani, and R. Fochi, Ann. Chim, (Roma), 57, 1045 (1967).

    Google Scholar 

  63. J. Degani, R. Fochi, and G. Spunta, Boll. Sci. Fac. Chim. Industr. Bologna, 23, 151 (1965).

    Google Scholar 

  64. S. V. Krivun and S. V. Dul'skaya, Khim. Geterotsikl. Soedin., 1454 (1970).

  65. J. Degani, R. Fochi, and G. Spunta, Boll. Sci. Fac. Chim. Industr. Bologna, 26, 31 (1968).

    Google Scholar 

  66. J. Degani and R. Fochi, Ann. Chim. (Roma), 58, 251 (1968).

    Google Scholar 

  67. S. N. Baranov, M. A. Ladovskaya, and S. V. Krivun, Khim. Geterotsikl. Soedin, 565 (1971).

  68. S. V. Krivun, Khim. Geterotsikl. Soedin., 14 (1971).

  69. S. V. Krivun, S. N. Baranov, and O. F. Voznyakova, Dokl. Akad. Nauk SSSR, 196, 600 (1971).

    Google Scholar 

  70. S. V. Krivun, O. F. Voznyakova, and S. N. Baranov, Zh. Obshch. Khim., 42, 58 (1972).

    Google Scholar 

  71. S. N. Baranov, I. A. Buryak, and S. V. Krivun, Dokl. Akad. Nauk Ukr. SSR, B, 629 (1971).

  72. E. J. Brown, D. Leaver, and D. M. Kinnon, J. Chem. Soc., 1202 (1970).

  73. A. I. Tolmachev and V. P. Sribnaya, Khim. Geterotsikl. Soedin., 183 (1966).

  74. K. Dimroth, Angew. Chem., 72, 331 (1960).

    Google Scholar 

  75. G. N. Dorofeenko, S. V. Krivun, V. I. Dulenko, and Yu. A. Zhdanov, Usp. Khim., 34, 219 (1965).

    Google Scholar 

  76. A. T. Balaban, W. Schoth, and G. Fischer, Adv. Heterocycl. Chem., 10, 241 (1969).

    Google Scholar 

  77. Z. Joshida, S. Joneda, H. Sugimoto, and T. Sugimoto, Tetrahedron, 27, 6083 (1971).

    Google Scholar 

  78. G. A. Reynolds and J. A. Allan, J. Heterocycl. Chem., 8, 301 (1971).

    Google Scholar 

  79. S. Joneda, T. Sugimoto, and Z. Joshida, Tetrahedron, 29, 2009 (1973).

    Google Scholar 

  80. Z. Joshida, T. Sugimoto, and S. Joneda, Tetrahedron, 28, 5873 (1972).

    Google Scholar 

  81. Z. Joshida, S. Joneda, and T. Sugimoto, Chem. Lett, 17 (1972).

  82. Z. Joshida, T. Sugimoto, and S. Joneda, Tetrahedron Lett., 4259 (1971).

  83. J. Degani and C. Vincenzi, Boll. Sci. Fac. Chim. Industr. Bologna, 25, 77 (1967).

    Google Scholar 

  84. V. A. Pal'chkov, Yu. A. Zhdanov, and G. N. Dorofeenko, Zh. Organ. Khim., 1, 1171 (1965).

    Google Scholar 

  85. J. E. Jones, US Patent No. 3,579,345 (1971); Ref. Zh. Khim., 8Zh733P (1972).

  86. E. J. Seus, US Patent No. 3,591,372 (1971); Ref. Zh. Kihm., 6N73P (1972).

  87. W. J. Stauden Mayer and J. Eleming, US Patent No. 3615418 (1971); Ref. Zh. Khim., 16N526P (1962).

  88. E. P. Gramza and J. Owens, US Patent No. 3615396 (1971); Ref. Zh. Khim., 20N682P (1972).

  89. E. P. Gramza, US Patent No. 3615415 (1971); Ref. Zh. Khim., 20N683P.

  90. V. G. Kharchenko and A. R. Yakoreva, USSR Author's Certificate No. 216747 (1968); Byul. Izobr., No. 15 (1968).

  91. V. G. Kharchenko, V. I. Kleimenova, and A. R. Yakoreva, Khim. Geterotsikl. Soedin., 900 (1970).

  92. U. Eisner and T. Krishnamurthy, J. Org. Chem., 37, 150 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. G. Chernyshevskii Saratov State University, USSR

    V. G. Kharchenko, S. N. Chalaya & T. M. Konovalova

Authors
  1. V. G. Kharchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. N. Chalaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. M. Konovalova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–161, February, 1975.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kharchenko, V.G., Chalaya, S.N. & Konovalova, T.M. Thiapyrylium salts (review). Chem Heterocycl Compd 11, 125–136 (1975). https://doi.org/10.1007/BF00471381

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00471381

Keywords

Search

Navigation