Skip to main content
SpringerLink
Log in

Phase transfer catalysis in the chemistry of heterocyclic compounds. A review

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

This review covers new data on the use of phase transfer catalysis in the chemistry of heterocyclic compounds. The following reactions are considered: alkylation, acylation, reactions with dihalocarbenes, preparations of ethers and esters, the formation of halo derivatives, oxidation and reduction, and isotope exchange. The advantages of phase transfer catalysis are examined and the prospects for its further development in heterocyclic chemistry are discussed.

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. C. M. Starks and C. Liotta, Phase Transfer Catalysis Principles and Techniques, Academic Press, New York-London (1978).

    Google Scholar 

  2. W. Weber and G. Gokel, Phase Transfer Catalysis in Organic Synthesis, Springer-Verlag, (1977).

  3. E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, Springer-Verlag, Chemie, Weinheim (1980).

    Google Scholar 

  4. G. O. Torosyan and S. L. Paravyan, Arm. Khim. Zh., 34, 351 (1981).

    Google Scholar 

  5. M. Makosza and M. Fedorynski, Zh. Vses. Khim. Ova. im. D. I. Mendeleeva, 24, 466 (1979).

    Google Scholar 

  6. H. Alper, Advances in Organometallic Chemistry, Vol. 19 (1981), p. 183.

    Google Scholar 

  7. E. V. Dehmlow, Chimia, 34, 12 (1980).

    Google Scholar 

  8. Y. Imai, J. Macromol. Sci. Chem., 15A, 833 (1981); Chem. Abstr., 94, 209211 (1981).

    Google Scholar 

  9. S. L. Regen, Angew. Chem. Int. Ed. Eng., 18, 421 (1979).

    Google Scholar 

  10. A. Akelah and D. C. Sherrington, Chem. Rev., 81, 557 (1981).

    Google Scholar 

  11. M. Makosza, in: Survey of Progress in Chemistry, Vol. 9 (1980), p. 1.

    Google Scholar 

  12. G. W. Gokel, Chemalog Hi-Lites, Vol. 5 (1981), p. 1; Chem. Abstr., 94, 207908 (1981).

    Google Scholar 

  13. R. Gallo, J. H. M. Dou, and P. Hassanaly, Bull. Soc. Chim. Belg., 90, 849 (1981).

    Google Scholar 

  14. B. Reuben and K. Sjoberg, CHEMTECH, Vol. 11 (1981), p. 315; Chem. Abstr., 94, 210766 (1981).

    Google Scholar 

  15. A. Lopez, M. T. Maurette, R. Martino, and A. Lattes, Tetrahedrom Lett., No. 23, 2013 (1978).

    Google Scholar 

  16. M. T. Maurette, A. Lopez, R. Martino, and A. Lattes, Compt. Rend., 282C, 599 (1976).

    Google Scholar 

  17. D. Reuschling, H. Pietsch, and A. Linkies, Tetrahedron Lett., No. 7, 615 (1978).

    Google Scholar 

  18. S. R. Fletcher and I. I. Kay, Chem. Commun., No. 20, 903 (1978).

    Google Scholar 

  19. T. Okawara, Y. Noguchi, T. Matsuda, and M. Furukawa, Chem. Lett., No. 2, 185 (1981).

    Google Scholar 

  20. H. Takahata, Y. Ohnishi, H. Takehara, K. Tsuritani, and T. Yamazaki, Chem. Pharm. Bull., 29, 1063 (1981).

    Google Scholar 

  21. W. C. Guida and D. J. Mathre, J. Org. Chem., 45, 3172 (1980).

    Google Scholar 

  22. A. Jonczyk and M. Makosza, Rocz. Chem., 49, 1203 (1975).

    Google Scholar 

  23. A. Barco, S. Benetti, G. P. Pollini, and P. G. Baraldi, Synthesis, No. 2, 124 (1976).

    Google Scholar 

  24. N. N. Suvorov, Yu. I. Smushkevich, V. S. Velezheva, V. S. Rozhkov, and S. V. Simakov, Khim. Geterotsikl. Soedin., No. 2, 191 (1976).

    Google Scholar 

  25. M. Makosza, K. Wojciechowski, and M. Jawdosiuk, Pol. J. Chem., 52, 1173 (1978).

    Google Scholar 

  26. J. Palecek and J. Kuthan, Z. Chem., 7, 260 (1977).

    Google Scholar 

  27. D. Landini and F. Rolla, Synthesis, No. 6, 389 (1976).

    Google Scholar 

  28. S. Julia, A. Ginebreda, and J. Guixer, Chem. Commun., No. 17, 642 (1978).

    Google Scholar 

  29. S. Julia, A. Ginebreda, J. Guixer, J. Masona, and A. Tomas, J. Chem. Soc. Perkin Trans. I, No. 2, 574 (1981).

    Google Scholar 

  30. F. Seela and H. Winkler, J. Org. Chem., 47, 226 (1982).

    Google Scholar 

  31. H. J. M. Dou and J. Metzger, Bull. Soc. Chim. Fr., No. 11, 1861 (1976).

    Google Scholar 

  32. P. Hassanaly, H. J. M. Dou, J. Metzger, G. Assef, and J. Kister, Synthesis, No. 4, 253 (1977).

    Google Scholar 

  33. H. J. M. Dou, M. Ludwikow, P. Hassanaly, J. Kister, and J. Metzger, J. Heterocycl. Chem., 17, 393 (1980).

    Google Scholar 

  34. G. Vernin, H. Demlog, C. Siv, J. Metzger, and A. K. El-Shotei, J. Heterocycl. Chem., 18, 85 (1981).

    Google Scholar 

  35. K. Kiec-Kononowicz, A. Zeijc, M. Mikolajczyk, A. Zatorski, J. Karolak-Wojciechlwksa, and M. W. Wieczorek, Tetrahedron, 37, 409 (1981).

    Google Scholar 

  36. G. Tarrago, A. Ramdani, J. Elguero, and M. Espada, J. Heterocycl. Chem., 17, 137 (1980).

    Google Scholar 

  37. H. J. M. Dou, P. Hassanaly, J. Kister, G. Vernin, and J. Metzger, Helv. Chim. Acta, 61, 3143 (1978).

    Google Scholar 

  38. H. J. M. Dou, P. Hassanaly, J. Metzger, J. Heterocycl. Chem., 14, 321 (1977).

    Google Scholar 

  39. J. A. Bristol, I. Gross, and R. G. Lovey, Synthesis, No. 12, 971 (1981).

    Google Scholar 

  40. J. Palecek and J. Kuthan, Synthesis, No. 8, 550 (1976).

    Google Scholar 

  41. I. Willner and M. Halpern, Synthesis, No. 3, 177 (1979).

    Google Scholar 

  42. J. P. Galy, J. Elguero, E. J. Vincent, A. M. Galy, and J. Barbe, Synthesis, No. 12, 944 (1979).

    Google Scholar 

  43. E. A. Runova, L. N. Borodina, A. I. Shcherbakov, and É. A. Karakhanov, Vestn. Mosk. Gos. Univ., 20, 581 (1979).

    Google Scholar 

  44. M. Hedayatullah, J. Heterocycl. Chem., 18, 339 (1981).

    Google Scholar 

  45. J. Golinski and M. Makosza, Synthesis, No. 11, 823 (1978).

    Google Scholar 

  46. J. Masse, Synthesis, No. 5, 341 (1977).

    Google Scholar 

  47. I. Shinkal, M. C. V. Zwan, F. W. Hartner, R. A. Reamer, R. J. Tull, and L. M. Weinstock, J. Heterocycl. Chem., 18, 197 (1981).

    Google Scholar 

  48. G. Vernin, H. Domloj, C. Siv, J. Metzger, A. Archavlis, and J. Llinas, Chem. Scr., No. 5, 157 (1980); Chem. Abstr., 95, 80909 (1981).

    Google Scholar 

  49. M. Makosza, M. Ludwikow, and A. Urniaz, Roczn. Chem., 49, 297 (1975).

    Google Scholar 

  50. M. Jawdosiuk, M. Makosza, E. Mallnowska, and W. Wilcznyski, Pol. J. Chem., 53, 613 (1979).

    Google Scholar 

  51. W. Wilczynski, M. Jawdosiuk, and M. Makosza, Roczn, Chem., 51, 1643 (1977).

    Google Scholar 

  52. S. Cabiddu, A. Maccioni, and M. Secci, Synthesis, No. 12, 797 (1976).

    Google Scholar 

  53. G. Coudert, G. Guillaumet, and B. Loubinoux, Synthesis, No. 7, 541 (1976).

    Google Scholar 

  54. V. O. Illi, Synthesis, No. 5, 387 (1979).

    Google Scholar 

  55. V. O. Illi, Synthesis, No. 2, 136 (1979).

    Google Scholar 

  56. A. M. Leusen and J. Wildeman, Synthesis, No. 7, 501 (1977).

    Google Scholar 

  57. Y. Watanabe and T. Mukaiyama, Chem. Lett., No. 4, 443 (1981).

    Google Scholar 

  58. A. R. Allan and M. Baird, Chem. Commun., No. 5, 172 (1975).

    Google Scholar 

  59. Y. Gaoni, Tetrahedron Lett., No. 25, 2167 (1976).

    Google Scholar 

  60. J. Graefe, M. Adler, and M. Muhlstadt, Z. Chem., 15, 14 (1975).

    Google Scholar 

  61. S. Kwon, Y. Nishimura, M. Ikeda, and Y. Tamura, Synthesis, No. 4, 249 (1976).

    Google Scholar 

  62. F. D. Angelis, A. Gambacorta, and R. Nicolleti, Synthesis, No. 12, 798 (1976).

    Google Scholar 

  63. P. Weyerstahl and G. Blume, Tetrahedron, 28, 5281 (1972).

    Google Scholar 

  64. G. Hofle, Z. Naturforsch., 28B, 831 (1973).

    Google Scholar 

  65. T. Saraie, T. Ishiguro, K. Kawashima, and K. Morita, Tetrahedron Lett., No. 23, 2121 (1973).

    Google Scholar 

  66. V. I. Boev, Zh. Org. Khim., 17, 1340 (1981).

    Google Scholar 

  67. J. Graefe, Z. Chem., 14, 469 (1974).

    Google Scholar 

  68. M. Makosza and A. Kacprowicz, Roczn. Chem., 48, 2129 (1974).

    Google Scholar 

  69. T. Sasaki, S. Eguchi, and T. Ogawa, Heterocycles, 3, 193 (1975).

    Google Scholar 

  70. A. McKillop, J. C. Fiaud, and R. P. Hug, Tetrahedron, 30, 1379 (1974).

    Google Scholar 

  71. A. Cornelis and P. Laszlo, Synthesis, No. 2, 162 (1982).

    Google Scholar 

  72. G. J. Rall, M. E. Oberholzer, D. Ferreira, and D. G. Roux, Tetrahedron Lett., No. 13, 1033 (1976).

    Google Scholar 

  73. G. A. Tolstikov, N. N. Novitskaya, and É. É. Shul'ts, Zh. Org. Khim., 18, 1301 (1982).

    Google Scholar 

  74. A. Bashall and. J. F. Collins, Tetrahedron Lett., No. 40, 3489 (1975).

    Google Scholar 

  75. H. Alsaidi, R. Gallo, and J. Metzger, Synthesis, No. 11, 921 (1980).

    Google Scholar 

  76. I. Bolmgren and T. Norin, Acta. Chem. Scand., 35B, 742 (1981).

    Google Scholar 

  77. V. S. Etlis, A. B. Bulovyatova, F. N. Shomina, and A. E. Semenova, Zh. Org. Chim., 18, 1830 (1982).

    Google Scholar 

  78. F. M. Menger, J. U. Rhee, and H. K. Rhee, J. Org. Chem., 40, 3803 (1975).

    Google Scholar 

  79. L. M. Rossi and P. Trimarco, Synthesis, No. 10, 743 (1978).

    Google Scholar 

  80. P. Kadaba, Synthesis, No. 9, 694 (1978).

    Google Scholar 

  81. R. M. Boden, Synthesis, No. 10, 783 (1975).

    Google Scholar 

  82. D. J. Raber and W. C. Guida, J. Org. Chem., 41, 690 (1976).

    Google Scholar 

  83. R. Helder, J. C. Hummelen, R. W. Laane, J. W. Wiering, and H. Wynberg, Tetrahedron Lett., No. 21, 1831 (1976).

    Google Scholar 

  84. I. Kuwajima, T. Murofushi, and E. Nakamura, Synthesis, No. 9, 602 (1976).

    Google Scholar 

  85. T. Wakabayashi and Y. Kato, Tetrahedron Lett., No. 14, 1235 (1977).

    Google Scholar 

  86. T. Sakakibara and R. Sudoh, J. Org. Chem., 40, 2823 (1975).

    Google Scholar 

  87. T. Sakakibara, M. Yamada, and R. Sudoh, J. Org. Chem., 41, 736 (1976).

    Google Scholar 

  88. L. Fitjer, Synthesis, No. 3, 189 (1977).

    Google Scholar 

  89. M. Gross and F. Peter. Bull. Soc. Chim. Fr., No. 3, 871 (1975).

    Google Scholar 

  90. W. J. Spillane, H. J. M. Dou, and J. Metzger, Tetrahedron Lett., No. 26, 2269 (1976).

    Google Scholar 

  91. W. J. Spillane, P. Kavanagh F. Young, H. J. M. Dou, and J. Metzger, J. Chem. Soc., Perkin Trans. I, No. 6, 1763 (1981).

    Google Scholar 

  92. A. Jonczyk, K. Banko, and M. Makosza, J. Org. Chem., 40, 266 (1975).

    Google Scholar 

  93. T. Hiyama, T. Mishima, H. Sawada, and H. Nozaki, J. Am. Chem. Soc., 97, 1626 (1975).

    Google Scholar 

  94. T. Hiyama, T. Mishima, H. Sawada, and H. Nozaki, J. Am. Chem. Soc., 98, 641 (1976).

    Google Scholar 

  95. P. B. Dervan and M. A. Shippey, J. Am. Chem. Soc., 98, 1265 (1976).

    Google Scholar 

  96. Y. Nakajima, R. Kinishi, J. Oda, and Y. Inouye, Bull. Chem. Soc. Jpn., 50, 2025 (1977).

    Google Scholar 

  97. M. Ellwood and J. Griffiths, Chem. Commun., No. 4, 181 (1980).

    Google Scholar 

  98. A. Kabori, M. Ohtori, and K. Azai, Bull. Chem. Soc. Jpn., 49, 746 (1976).

    Google Scholar 

  99. G. A. Tolstikov, N. N. Novitskaya, and É. É. Shul'ts, J. Org. Khim., 18, 1307 (1982).

    Google Scholar 

  100. S. E. Lauritzen, C. Romming, and L. Skattebol, Acta. Chem. Scand., 35B, 263 (1981).

    Google Scholar 

  101. V. Dryanska and C. Ivanov, Tetrahedron Lett., No. 41, 3519 (1975).

    Google Scholar 

  102. G. W. Gokel, S. A. Dibiase, and V. A. Lipisko, Tetrahedrom Lett., No. 39, 3495 (1976).

    Google Scholar 

  103. C. Piechuki, Synthesis, No. 3, 187 (1976).

    Google Scholar 

  104. P. K. Jain, J. K. Makrandi, and S. K. Grover, Synthesis, No. 3, 221 (1982).

    Google Scholar 

  105. J. M. McIntosh and H. Khalil, J. Org. Chem., 42, 2123 (1977).

    Google Scholar 

  106. G. W. Gokel, H. M. Gerdes, and N. W. Rebert, Tetrahedron Lett., No. 9, 653 (1976).

    Google Scholar 

  107. R. W. Ridgway, H. S. Greenside, and H. H. Freedman, J. Am. Chem. Soc., 98, 1979 (1976).

    Google Scholar 

  108. J. M. McIntosh, Tetrahedron, 38, 261 (1982).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lensovet Leningrad Technological Institute, 198013, Leningrad

    G. I. Koldobskii, V. A. Ostrovskii & T. F. Osipova

Authors
  1. G. I. Koldobskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Ostrovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. F. Osipova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1443–1459, November, 1983.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koldobskii, G.I., Ostrovskii, V.A. & Osipova, T.F. Phase transfer catalysis in the chemistry of heterocyclic compounds. A review. Chem Heterocycl Compd 19, 1141–1154 (1983). https://doi.org/10.1007/BF00515343

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00515343

Keywords

Search

Navigation