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Phase-Transfer Catalysis: Fundamentals II

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Phase-Transfer Catalysis

Abstract

Phase-transfer catalytic (PTC) systems are characterized by the presence of at least two phases and at least one interfacial region separating the phases [1–8]. Reactions taking place in such systems usually involve (1) transfer of an anionic reactant from its “normal” phase into the reaction phase or interfacial region, (2) reaction of the transferred anion with the nontransferred reactant located in the reaction phase or interfacial region, and (3) transfer of the anionic product from the reaction phase or interfacial region into its “normal” phase. Thus, PTC reactions involve several steps occurring in series and/or in parallel. As a consequence, a quantitative description of the entire process necessitates defining the reactions and corresponding rates taking place within each of the phases and within the interfacial region, and the rates of mass transfer of the reactant and product anions into and through the interfacial region.

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References

  1. W.P. Weber and G. W. Gokel, Phase Transfer Catalysis in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York (1977).

    Book  Google Scholar 

  2. C.M. Starks and C.L. Liotta, Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York (1978).

    Google Scholar 

  3. E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, 2nd ed; Verlag Chemie: Weinheim (1983).

    Google Scholar 

  4. F. Montanari, D. Landini and F. Rolla, Top. Curr. Chem., 101, 147 (1982).

    Article  CAS  Google Scholar 

  5. A. Brandstrom, Principles of Phase Transfer Catalysis by Quaternary Ammonium Salts, in Advances in Physical Organic Chemistry, Academic Press, London and New York (1977).

    Google Scholar 

  6. E.V. Dehmlow, Angew, Chem., Int. Ed. Engl., 16, 493 (1977).

    Article  Google Scholar 

  7. M. Makosza, In Survey of Progress in Chemistry, A.F. Scott, ed., Academic Press, New York, 1 (1980).

    Chapter  Google Scholar 

  8. H.H. Freedman, Pure Appl. Chem., 58, 857 (1986).

    Article  CAS  Google Scholar 

  9. C.M. Starks, J. Am. Chem. Soc, 93, 195 (1971).

    Article  CAS  Google Scholar 

  10. C.M. Starks and D.R. Napier, U.S. Patent 3,992,432 (1976)

    Google Scholar 

  11. C.M. Starks and D.R. Napier, British Patent 1,227,144 (1971)

    Google Scholar 

  12. C.M. Starks and D.R. Napier, French Patent 1,573,164 (1969)

    Google Scholar 

  13. C.M. Starks and D.R. Napier, Australian Patent 439,286 (1968)

    Google Scholar 

  14. C.M. Starks and D.R. Napier, Netherlands Patent 6,804,687, (1968).

    Google Scholar 

  15. C.M. Starks and R.M. Owens, J. Am. Chem. Soc., 95, 3613 (1973).

    Article  CAS  Google Scholar 

  16. D. Landini, A. Maia, and F. Montanari, J. Chem. Soc. Chem. Comm., 112 (1977).

    Google Scholar 

  17. M. Makosza, Pure Appl. Chem., 43, 439 (1975).

    Article  CAS  Google Scholar 

  18. M. Makosza, Russ. Chem. Rev., 46, 1151 (1977).

    Article  Google Scholar 

  19. M. Makosza and E. Bialecka, Tetrahedron Lett., 2, 1983 (1977).

    Google Scholar 

  20. A.M. Tivert and K. Gustavil, Acta Pharm. Suec, 16, 1 (1979).

    CAS  Google Scholar 

  21. A.W. Herriott and D.H. Picker, J. Am. Chem. Soc, 97 (1975).

    Google Scholar 

  22. C.L. Liotta, E.M. Burgess, C.C. Ray, E.D. Black, and B.E. Fair, ACS Symp. Ser., No. 326. 15 (1987).

    Google Scholar 

  23. D. Landini, A.M. Maia, F. Montanari, and F.M. Pirisi, J. Chem. Soc. Chem. Comm., 950 (1975).

    Google Scholar 

  24. D. Landini, A. Maia, and F. Montanari, J. Am. Chem. Soc, 100, 2796 (1978).

    Article  CAS  Google Scholar 

  25. H.H. Freedman and R.A. Dubois, Tetrahedron Lett., 3251 (1975).

    Google Scholar 

  26. T-C. Huang and S-C Lin, J. Chin, Ch. E., 19, 193 (1988).

    CAS  Google Scholar 

  27. M-Y. Yeh, H-H. Guo, L-C. Chen, and Y-P. Shih, Ind. Eng. Chem. Res., 27, 1582 (1988).

    Article  CAS  Google Scholar 

  28. J-R. Chang, M-Y. Yeh, and Y-P. Shih, J. Chim Chem. Soc., 31, 185 (1984)

    CAS  Google Scholar 

  29. J-R. Chang, M-Y. Yeh, and Y-P. Shih, J. Chin. Ch. E., 14, 457 (1983).

    CAS  Google Scholar 

  30. M-L. Wang and H-S. Wu, J. Org. Chem., 55, 2344 (1990).

    Article  CAS  Google Scholar 

  31. M-L. Wang and H-S Wu, J. Chem. Soc Perkin Trans. 2, 841 (1991).

    Google Scholar 

  32. M-L. Wang and H-S. Wu, Chemical Engineering Science, 46, 509 (1991).

    Article  CAS  Google Scholar 

  33. W.F. Lunder, P.B. Kraus, and R.M. Fuoss, J. Am. Chem. Soc., 58, 225 (1936).

    Article  Google Scholar 

  34. E.D. Hughes, C.K. Ingold, S. Patai and Y. Pocker, J. Chem. Soc., 1209 (1957).

    Google Scholar 

  35. M.J. McDowell and C.A. Draus, Tetrahedron Lett., 3251 (1975).

    Google Scholar 

  36. A. Brandstrom and H. Kolind-Anderson, Acta Chem Scand., 29B, 201 (1975).

    Article  Google Scholar 

  37. A. Brandstrom, Acta Chem. Scand., 30B, 203 (1976).

    Article  Google Scholar 

  38. J. Uglestad, T. Ellingsen, and A. Beige, Acta Chem. Scand., 20, 1593 (1966).

    Article  Google Scholar 

  39. L. Pauling, The Nature of the Chemical Bond, Appendix 3.1, Cornell Univ. Press, Ithaca, New York (1940).

    Google Scholar 

  40. B.E. Conway, R.E. Verall, and J.E. Desnoyers, Trans, Faraday Soc., 62, 2738 (1966); and references contained therein.

    Article  CAS  Google Scholar 

  41. T.C. Pochapsky and P.M. Stone, J. Am. Chem. Soc., 112, 6714 (1990).

    Article  CAS  Google Scholar 

  42. T.C. Pochapsky, P.M. Stone, and S.S. Pochapsky, J. Am. Chem. Soc., 113, 1460 (1991).

    Article  CAS  Google Scholar 

  43. R. Alexander and A.J. Parker, J. Am. Chem. Soc., 89, 5549 (1967).

    Article  CAS  Google Scholar 

  44. J.H. Ramsden, R.S. Drago, and R. Riley, J. Am. Chem. Soc., 111, 3958 (1989).

    Article  CAS  Google Scholar 

  45. M. Rabinovitz, Y. Cohen, and M. Halpern, Angew, Chem., Int. Ed., Engl., 25, 960 (1986); and references contained therein.

    Article  Google Scholar 

  46. N.A. Gibson and D.C. Weatherburn, Anal. Cheim. Acta, 58, 160 (1972).

    Google Scholar 

  47. J.P. Antoine, I.F. de Aguirre, F. Janssons, and F. Thyrion, Bull. Soc. Chim. Fr., 207 (1980).

    Google Scholar 

  48. K. Gustavii and G. Shill, Acta Pharm. Suec., 3, 241 (1966).

    CAS  Google Scholar 

  49. K. Gustavii, Acta. Pharm. Suec., 4, 233 (1967).

    CAS  Google Scholar 

  50. D. Mason, S. Magdassi, and Y. Sasson, J. Org. Chem., 55, 2714 (1990).

    Article  CAS  Google Scholar 

  51. A.E. Vassiliades, In Surfactant Science; Marcel Dekker, New York, 1970; Series Vol. 4, Chapter 12.

    Google Scholar 

  52. Y. Sela and S. Magdassi, Tenside, 27, 179 (1990).

    CAS  Google Scholar 

  53. D. Mason, S. Magdassi, and Y. Sasson, J. Org. Chem., 56, 7229 (1991).

    Article  CAS  Google Scholar 

  54. D.H. Wang and H.S. Weng, Chem. Eng. Sci., 43, 2019 (1988).

    Article  CAS  Google Scholar 

  55. R. Neumann and Y. Sasson, J. Org. Chem., 49, 3448 (1984).

    Article  CAS  Google Scholar 

  56. M. Halpern, Y. Cohen, Y. Sasson, and M. Rabinovitz, Nouv. J. Chim., 8, 443 (1984).

    CAS  Google Scholar 

  57. C.L. Liotta and J. Hurley, unpublished results.

    Google Scholar 

  58. A. Merz, Angew, Chem., 85, 868 (1973).

    Article  CAS  Google Scholar 

  59. A. Merz, Angew, Chem. Int. Ed. Engl., 11, 846 (1973).

    Article  Google Scholar 

  60. R. Solaro, S. D’Antone, and E. Chielline, J. Org. Chem., 45, 4179 (1980).

    Article  CAS  Google Scholar 

  61. M. Halpern, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 47, 1022 (1983).

    Article  Google Scholar 

  62. D. Landini, A. Maia, and A. Rampoli, J. Org. Chem., 51, 3187 (1986).

    Article  CAS  Google Scholar 

  63. J. Fitzjohn, private communication.

    Google Scholar 

  64. D. Landini and A. Maia, J. Chem. Soc., Chem. Commun., 1041 (1984).

    Google Scholar 

  65. D.K. Bohme and G.I. Mackay, J. Am. Chem. Soc., 103, 978 (1981).

    Article  CAS  Google Scholar 

  66. J. Dockx, Synthesis, 441 (1973).

    Google Scholar 

  67. A. Gorgoes, A. Le Coq, Tetrahedron Lett., 4521 (1976).

    Google Scholar 

  68. K. Seenewald, K. Gehrmann, and G. Viertel, German Patent 1,271,107 (1968).

    Google Scholar 

  69. E.F. Lutz, J.T. Kelly, and D.W. Hall, British Patent 1,112,068 (1968).

    Google Scholar 

  70. E.V. Dehmlow and M. Lissel, Tetrahedron, 37, 1653 (1981).

    Article  CAS  Google Scholar 

  71. D. Landini and A. Maia, J. Chem. Soc., Chem. Comm., 1041 (1984).

    Google Scholar 

  72. E.V. Dehmlow, M. Slopianka, and J. Heider, Tetrahedron Lett., 2361 (1977).

    Google Scholar 

  73. E.V. Dehmlow, R. Thieser, Y. Sasson, and E. Pross, Tetrahedron, 41, 2972 (1985).

    Article  Google Scholar 

  74. M. Halpern, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 49, 2011 (1984).

    Article  CAS  Google Scholar 

  75. M. Halpern, H.A. Zahalka, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 50, 5088 (1985).

    Article  CAS  Google Scholar 

  76. M. Ellwood, J. Griffiths, and P. Gregory, Chem. Commun., 181 (1980).

    Google Scholar 

  77. H. Iwamoto, T. Sonoda, and H. Kobayashi, Tetrahedron Lett., 4703 (1983).

    Google Scholar 

  78. H. Kobayashi, T. Sonoda, and H. Iwamoto, Chem. Lett., 1185 (1982).

    Google Scholar 

  79. R.K. Smalley and H. Suschitzky, J. Chem. Soc., 775 (1964).

    Google Scholar 

  80. M. Yamada, Y. Watabe, T. Sakakibara, and R. Sudoh, J. Chem. Soc., Chem. Commun., 179 (1979).

    Google Scholar 

  81. L.J. Mathias and R.A. Vaidya, J. Am. Chem. Soc., 108, 1093 (1986).

    Article  CAS  Google Scholar 

  82. W.K. Fife and Y. Xin, J. Am. Chem. Soc., 109, 1278 (1987); and references contained therein.

    Article  CAS  Google Scholar 

  83. C-S. Kuo and J-J. Jwo, J. Org. Chem., 57, 1991 (1992).

    Article  CAS  Google Scholar 

  84. D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 94, 4024 (1972).

    Article  CAS  Google Scholar 

  85. C.L. Liotta and H.P. Harris, J. Am. Chem. Soc., 96, 2250 (1974).

    Article  CAS  Google Scholar 

  86. D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 96, 2252 (1974).

    Article  CAS  Google Scholar 

  87. F.L. Cook, C.W. Bowers and C.L. Liotta, J. Org. Chem., 39, 3416 (1974).

    Article  CAS  Google Scholar 

  88. C.L. Liotta, et al. Tetrahedron Lett., 28, 2417 (1974).

    Article  Google Scholar 

  89. J. Barry, et al. Tetrahedron Lett., 23, 5407 (1982)

    CAS  Google Scholar 

  90. J. Barry, et al. J. Org. Chem., 49, 1138 (1984)

    Article  CAS  Google Scholar 

  91. J. Barry, et al., Synthesis 40 (1985).

    Google Scholar 

  92. G. Bram, et al. Synth. Commun., 49, 1138 (1984)

    Google Scholar 

  93. G. Bram, and G. Decodts, Synthesis, 543 (1985)

    Google Scholar 

  94. G. Bram, A. Loupy, and J. Sansoulet, Israel J. Chem., 26, 291 (1985).

    CAS  Google Scholar 

  95. P. Singh, M.S. Batra, and H. Singh, J. Chem. Res. (S), 204 (1985).

    Google Scholar 

  96. M.C. Vander Zwan and F.W. Hartner, J. Org. Chem., 43, 2655 (1978).

    Article  Google Scholar 

  97. H.A. Yee, J.J. Palmer, and S.H. Chen, Chem. Engin. Prog., 33 (1987).

    Google Scholar 

  98. J.B. Melville, and J.D. Goddard, Ind. Eng. Chem. Res., 27, 551 (1988)

    Article  CAS  Google Scholar 

  99. J.B. Melville, and J.D. Goddard, Chem. Engin. Sci., 40, 2207 (1985).

    Article  CAS  Google Scholar 

  100. K. Wong and A.P.W. Wai, J. Chem. Soc. Perkin Trans., 11, 317 (1983).

    Google Scholar 

  101. E.V. Dehmlow, Tetrahedon Lett., 91 (1976)

    Google Scholar 

  102. E.V. Dehmlow and T. Remmler, J. Chem. Res. (S), 72 (1977).

    Google Scholar 

  103. H.A. Zahalka, and Y. Sasson, J. Chem. Soc. Chem. Commun., 1652 (1984).

    Google Scholar 

  104. S. Deremik and Y. Sasson, J. Org. Chem., 47, 2264 (1985).

    Google Scholar 

  105. Y. Sasson, and H.A. Zahalka, J. Chem. Soc., Chem. Commun., 1347 (1983).

    Google Scholar 

  106. D. Landini, A.M. Maia, and G. Podda, J. Org. Chem., 47, 2264 (1982).

    Article  CAS  Google Scholar 

  107. O.I. Danilova, I.A. Esikova, and S.S. Yufit, Izv. Akad. Nauk SSSR, Ser. Khim., 314 (1988)

    Google Scholar 

  108. O.I. Danilova, I.A. Esikova, and S.S. Yufit, Chem. Abstr., 109, 169773j (1988).

    Google Scholar 

  109. S.S. Yufit, I.A. Esikova, and O.I. Danilova, Dokl. Akad. Nauk SSSR., 295, 621 (1987).

    CAS  Google Scholar 

  110. O. Arad and Y. Sasson, J. Am. Chem. Soc, 110, 185 (1988).

    Article  Google Scholar 

  111. E.V. Dehmlow and H.J. Rarhs, J. Chem. Res. (S), 384 (1988).

    Google Scholar 

  112. C.L. Liotta, Application of Macrocyclic Polydentate Ligands to Synthetic Transformations, in Synthetic Multidentate Macrocyclic Compounds, R.M. Izatt, J.J. Christensen, eds. Academic Press, New York, p. 111 (1978).

    Chapter  Google Scholar 

  113. S.S. Yufit and I.A. Esikova, J. Phys. Org. Chem., 4, 336 (1991).

    Article  CAS  Google Scholar 

  114. I.A. Esikova and S.S. Yufit, Izv. Akad, Nauk SSSR, Ser, Khim. 1524 (1988)

    Google Scholar 

  115. I.A. Esikova and S.S. Yufit, Chem. Abstr., 110, 94247a (1989).

    Google Scholar 

  116. I.A. Esikova and S.S. Yufit, J. Phys. Org. Chem., 4, 149 (1991).

    Article  CAS  Google Scholar 

  117. I.A. Esikova and S.S. Yufit, J. Phys. Org. Chem., 4, 341 (1991).

    Article  CAS  Google Scholar 

  118. J.W. Zubrick, B.I. Dunbar, and H.D. Durst, Tetrahedron Lett., 1, 71 (1975).

    Article  Google Scholar 

  119. C.L. Liotta, E.M. Burgess, and E.D. Black, Polymer Preprints, 31, 65 (1990).

    Google Scholar 

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Starks, C.M., Liotta, C.L., Halpern, M.E. (1994). Phase-Transfer Catalysis: Fundamentals II. In: Phase-Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0687-0_3

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