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
W.P. Weber and G. W. Gokel, Phase Transfer Catalysis in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, New York (1977).
C.M. Starks and C.L. Liotta, Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York (1978).
E.V. Dehmlow and S.S. Dehmlow, Phase Transfer Catalysis, 2nd ed; Verlag Chemie: Weinheim (1983).
F. Montanari, D. Landini and F. Rolla, Top. Curr. Chem., 101, 147 (1982).
A. Brandstrom, Principles of Phase Transfer Catalysis by Quaternary Ammonium Salts, in Advances in Physical Organic Chemistry, Academic Press, London and New York (1977).
E.V. Dehmlow, Angew, Chem., Int. Ed. Engl., 16, 493 (1977).
M. Makosza, In Survey of Progress in Chemistry, A.F. Scott, ed., Academic Press, New York, 1 (1980).
H.H. Freedman, Pure Appl. Chem., 58, 857 (1986).
C.M. Starks, J. Am. Chem. Soc, 93, 195 (1971).
C.M. Starks and D.R. Napier, U.S. Patent 3,992,432 (1976)
C.M. Starks and D.R. Napier, British Patent 1,227,144 (1971)
C.M. Starks and D.R. Napier, French Patent 1,573,164 (1969)
C.M. Starks and D.R. Napier, Australian Patent 439,286 (1968)
C.M. Starks and D.R. Napier, Netherlands Patent 6,804,687, (1968).
C.M. Starks and R.M. Owens, J. Am. Chem. Soc., 95, 3613 (1973).
D. Landini, A. Maia, and F. Montanari, J. Chem. Soc. Chem. Comm., 112 (1977).
M. Makosza, Pure Appl. Chem., 43, 439 (1975).
M. Makosza, Russ. Chem. Rev., 46, 1151 (1977).
M. Makosza and E. Bialecka, Tetrahedron Lett., 2, 1983 (1977).
A.M. Tivert and K. Gustavil, Acta Pharm. Suec, 16, 1 (1979).
A.W. Herriott and D.H. Picker, J. Am. Chem. Soc, 97 (1975).
C.L. Liotta, E.M. Burgess, C.C. Ray, E.D. Black, and B.E. Fair, ACS Symp. Ser., No. 326. 15 (1987).
D. Landini, A.M. Maia, F. Montanari, and F.M. Pirisi, J. Chem. Soc. Chem. Comm., 950 (1975).
D. Landini, A. Maia, and F. Montanari, J. Am. Chem. Soc, 100, 2796 (1978).
H.H. Freedman and R.A. Dubois, Tetrahedron Lett., 3251 (1975).
T-C. Huang and S-C Lin, J. Chin, Ch. E., 19, 193 (1988).
M-Y. Yeh, H-H. Guo, L-C. Chen, and Y-P. Shih, Ind. Eng. Chem. Res., 27, 1582 (1988).
J-R. Chang, M-Y. Yeh, and Y-P. Shih, J. Chim Chem. Soc., 31, 185 (1984)
J-R. Chang, M-Y. Yeh, and Y-P. Shih, J. Chin. Ch. E., 14, 457 (1983).
M-L. Wang and H-S. Wu, J. Org. Chem., 55, 2344 (1990).
M-L. Wang and H-S Wu, J. Chem. Soc Perkin Trans. 2, 841 (1991).
M-L. Wang and H-S. Wu, Chemical Engineering Science, 46, 509 (1991).
W.F. Lunder, P.B. Kraus, and R.M. Fuoss, J. Am. Chem. Soc., 58, 225 (1936).
E.D. Hughes, C.K. Ingold, S. Patai and Y. Pocker, J. Chem. Soc., 1209 (1957).
M.J. McDowell and C.A. Draus, Tetrahedron Lett., 3251 (1975).
A. Brandstrom and H. Kolind-Anderson, Acta Chem Scand., 29B, 201 (1975).
A. Brandstrom, Acta Chem. Scand., 30B, 203 (1976).
J. Uglestad, T. Ellingsen, and A. Beige, Acta Chem. Scand., 20, 1593 (1966).
L. Pauling, The Nature of the Chemical Bond, Appendix 3.1, Cornell Univ. Press, Ithaca, New York (1940).
B.E. Conway, R.E. Verall, and J.E. Desnoyers, Trans, Faraday Soc., 62, 2738 (1966); and references contained therein.
T.C. Pochapsky and P.M. Stone, J. Am. Chem. Soc., 112, 6714 (1990).
T.C. Pochapsky, P.M. Stone, and S.S. Pochapsky, J. Am. Chem. Soc., 113, 1460 (1991).
R. Alexander and A.J. Parker, J. Am. Chem. Soc., 89, 5549 (1967).
J.H. Ramsden, R.S. Drago, and R. Riley, J. Am. Chem. Soc., 111, 3958 (1989).
M. Rabinovitz, Y. Cohen, and M. Halpern, Angew, Chem., Int. Ed., Engl., 25, 960 (1986); and references contained therein.
N.A. Gibson and D.C. Weatherburn, Anal. Cheim. Acta, 58, 160 (1972).
J.P. Antoine, I.F. de Aguirre, F. Janssons, and F. Thyrion, Bull. Soc. Chim. Fr., 207 (1980).
K. Gustavii and G. Shill, Acta Pharm. Suec., 3, 241 (1966).
K. Gustavii, Acta. Pharm. Suec., 4, 233 (1967).
D. Mason, S. Magdassi, and Y. Sasson, J. Org. Chem., 55, 2714 (1990).
A.E. Vassiliades, In Surfactant Science; Marcel Dekker, New York, 1970; Series Vol. 4, Chapter 12.
Y. Sela and S. Magdassi, Tenside, 27, 179 (1990).
D. Mason, S. Magdassi, and Y. Sasson, J. Org. Chem., 56, 7229 (1991).
D.H. Wang and H.S. Weng, Chem. Eng. Sci., 43, 2019 (1988).
R. Neumann and Y. Sasson, J. Org. Chem., 49, 3448 (1984).
M. Halpern, Y. Cohen, Y. Sasson, and M. Rabinovitz, Nouv. J. Chim., 8, 443 (1984).
C.L. Liotta and J. Hurley, unpublished results.
A. Merz, Angew, Chem., 85, 868 (1973).
A. Merz, Angew, Chem. Int. Ed. Engl., 11, 846 (1973).
R. Solaro, S. D’Antone, and E. Chielline, J. Org. Chem., 45, 4179 (1980).
M. Halpern, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 47, 1022 (1983).
D. Landini, A. Maia, and A. Rampoli, J. Org. Chem., 51, 3187 (1986).
J. Fitzjohn, private communication.
D. Landini and A. Maia, J. Chem. Soc., Chem. Commun., 1041 (1984).
D.K. Bohme and G.I. Mackay, J. Am. Chem. Soc., 103, 978 (1981).
J. Dockx, Synthesis, 441 (1973).
A. Gorgoes, A. Le Coq, Tetrahedron Lett., 4521 (1976).
K. Seenewald, K. Gehrmann, and G. Viertel, German Patent 1,271,107 (1968).
E.F. Lutz, J.T. Kelly, and D.W. Hall, British Patent 1,112,068 (1968).
E.V. Dehmlow and M. Lissel, Tetrahedron, 37, 1653 (1981).
D. Landini and A. Maia, J. Chem. Soc., Chem. Comm., 1041 (1984).
E.V. Dehmlow, M. Slopianka, and J. Heider, Tetrahedron Lett., 2361 (1977).
E.V. Dehmlow, R. Thieser, Y. Sasson, and E. Pross, Tetrahedron, 41, 2972 (1985).
M. Halpern, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 49, 2011 (1984).
M. Halpern, H.A. Zahalka, Y. Sasson, and M. Rabinovitz, J. Org. Chem., 50, 5088 (1985).
M. Ellwood, J. Griffiths, and P. Gregory, Chem. Commun., 181 (1980).
H. Iwamoto, T. Sonoda, and H. Kobayashi, Tetrahedron Lett., 4703 (1983).
H. Kobayashi, T. Sonoda, and H. Iwamoto, Chem. Lett., 1185 (1982).
R.K. Smalley and H. Suschitzky, J. Chem. Soc., 775 (1964).
M. Yamada, Y. Watabe, T. Sakakibara, and R. Sudoh, J. Chem. Soc., Chem. Commun., 179 (1979).
L.J. Mathias and R.A. Vaidya, J. Am. Chem. Soc., 108, 1093 (1986).
W.K. Fife and Y. Xin, J. Am. Chem. Soc., 109, 1278 (1987); and references contained therein.
C-S. Kuo and J-J. Jwo, J. Org. Chem., 57, 1991 (1992).
D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 94, 4024 (1972).
C.L. Liotta and H.P. Harris, J. Am. Chem. Soc., 96, 2250 (1974).
D.J. Sam and H.F. Simmons, J. Am. Chem. Soc., 96, 2252 (1974).
F.L. Cook, C.W. Bowers and C.L. Liotta, J. Org. Chem., 39, 3416 (1974).
C.L. Liotta, et al. Tetrahedron Lett., 28, 2417 (1974).
J. Barry, et al. Tetrahedron Lett., 23, 5407 (1982)
J. Barry, et al. J. Org. Chem., 49, 1138 (1984)
J. Barry, et al., Synthesis 40 (1985).
G. Bram, et al. Synth. Commun., 49, 1138 (1984)
G. Bram, and G. Decodts, Synthesis, 543 (1985)
G. Bram, A. Loupy, and J. Sansoulet, Israel J. Chem., 26, 291 (1985).
P. Singh, M.S. Batra, and H. Singh, J. Chem. Res. (S), 204 (1985).
M.C. Vander Zwan and F.W. Hartner, J. Org. Chem., 43, 2655 (1978).
H.A. Yee, J.J. Palmer, and S.H. Chen, Chem. Engin. Prog., 33 (1987).
J.B. Melville, and J.D. Goddard, Ind. Eng. Chem. Res., 27, 551 (1988)
J.B. Melville, and J.D. Goddard, Chem. Engin. Sci., 40, 2207 (1985).
K. Wong and A.P.W. Wai, J. Chem. Soc. Perkin Trans., 11, 317 (1983).
E.V. Dehmlow, Tetrahedon Lett., 91 (1976)
E.V. Dehmlow and T. Remmler, J. Chem. Res. (S), 72 (1977).
H.A. Zahalka, and Y. Sasson, J. Chem. Soc. Chem. Commun., 1652 (1984).
S. Deremik and Y. Sasson, J. Org. Chem., 47, 2264 (1985).
Y. Sasson, and H.A. Zahalka, J. Chem. Soc., Chem. Commun., 1347 (1983).
D. Landini, A.M. Maia, and G. Podda, J. Org. Chem., 47, 2264 (1982).
O.I. Danilova, I.A. Esikova, and S.S. Yufit, Izv. Akad. Nauk SSSR, Ser. Khim., 314 (1988)
O.I. Danilova, I.A. Esikova, and S.S. Yufit, Chem. Abstr., 109, 169773j (1988).
S.S. Yufit, I.A. Esikova, and O.I. Danilova, Dokl. Akad. Nauk SSSR., 295, 621 (1987).
O. Arad and Y. Sasson, J. Am. Chem. Soc, 110, 185 (1988).
E.V. Dehmlow and H.J. Rarhs, J. Chem. Res. (S), 384 (1988).
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).
S.S. Yufit and I.A. Esikova, J. Phys. Org. Chem., 4, 336 (1991).
I.A. Esikova and S.S. Yufit, Izv. Akad, Nauk SSSR, Ser, Khim. 1524 (1988)
I.A. Esikova and S.S. Yufit, Chem. Abstr., 110, 94247a (1989).
I.A. Esikova and S.S. Yufit, J. Phys. Org. Chem., 4, 149 (1991).
I.A. Esikova and S.S. Yufit, J. Phys. Org. Chem., 4, 341 (1991).
J.W. Zubrick, B.I. Dunbar, and H.D. Durst, Tetrahedron Lett., 1, 71 (1975).
C.L. Liotta, E.M. Burgess, and E.D. Black, Polymer Preprints, 31, 65 (1990).
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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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DOI: https://doi.org/10.1007/978-94-011-0687-0_3
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