Abstract
Phase-transfer catalysis, also often referred to as “ion pair partition” is a novel synthetic technique which has been the subject of much interest in recent years not only in the field of organic synthesis but also in polymer chemistry. The term “phase-transfer catalysis” was first introduced in 1971 by Stark1,2 who studied kinetics in detail and the mechanism of reactions which are catalyzed by small amounts of onium salts such as quaternary ammonium or phosphonium compounds. Brändström3–5 and Makosza6–8 also made major initial contributions in the understanding of such reactions and the application thereof in various synthetic reactions. A generally accepted phase-transfer reaction scheme is shown in Fig. 1 for the reaction of RX + Y-→ RY + X-. Catalytic onium ion (Q+) transfers the nucleophile Y- into the organic phase in the form of ion pair Q+Y-, which then reacts with RX in organic phase producing the products RY and X-. X-’s are removed by Q+ from organic phase into aqueous phase as they are formed.
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References
C.M. Starks, J. Amer. Chem. Soc., 93 (1), 195 (1971).
C.M. Starks and R.M. Owens, J. Amer. Chem. Soc., 95 (11), 3613 (1973).
A. Brändström and U. Junggren, Acta Chem. Scand., 23, 2203, 2204, 2536, 3585 (1969); ibid, 25, 1469 (1971).
A. Brändström and K. Gustavii, Acta Chem. Scand., 23, 1215 (1969).
A. Brändström, K. Gustavii, and S. Allanson, Acta Chem. Scand., 25, 77 (1971).
M. Makosza, Tetrahedron Lett., 673, 677 (1969).
M. Makosza and W. Wawrzyniewicz, Tetrahedron Lett., 4659 (1969).
M. Makosza and E. Bialecka, Tetrahedron Lett., 4517 (1971).
C.J. Pedersen, J. Amer. Chem. Soc., 89, 7017 (1967).
B. Dietrich, J.M. Lehn, and J.P. Sauvage, Tetrahedron Lett, 2885, 2889 (1969).
J.M. Lehn, U.S. Pat., 3, 888, 877 (1975).
R.M. Izatt and J.J. Christensen, Eds., “Synthetic Multidentate Macrocyclic Compounds,” Academic Press, New York, 1978.
H.K. Frensdorff, J. Amer. Chem. Soc., 93 (3), 600 (1971).
L.J. Mathias, J. Macromol. Sci.-Chem., A15 (5), 853 (1981).
Y. Imai, J. Macromol. Sci.-Chem., A15 (5), 833 (1981).
J.-I. Jin, Y.-W. Jung, K.-S. Lee, and K.-W. Chung, J. Korean Chem. Sec., 24 (3), 259 (1979).
M. Hirose and Y. Immamura, Nippon Kagaku Zasshi, 1, 113 (1977).
K. Soga, S. Hosoda, and S. Ikeda, J. Polym. Sci.: Polym. Chem. Ed., 17, 517 (1979).
Y. Imai, M. Ueda, and M. Ii, Makromol, Chem., 179, 2085 (1978).
Y. Imai, A. Kato, M. Ii, and M. Ueda, J. Polym. Sci.: Polym. Lett. Ed., 17, 579 (1979).
A.K. Banthia, D. Lunsford, D.C. Webster, and J.E. McGrath, J. Macromol. Sci.-Chem., A15 (5), 946 (1981).
J.S. Riffle, R.G. Freelin, A.K. Banthia, and J.E. McGrath, J. Makromol. Sci.-Chem., A15 (5), 967 (1981).
D.J. Gerbi, R.F. Williams, R. Kellman, and J.L. Morgan, Polym. Preprints, 22 (2), 385 (1981).
H. Schnell, Angew. Chem., 68, 633 (1954).
P.W. Morgan, Macromolecules, 5, 536 (1970).
J.-I. Jin, K.-S. Lee, J.-H. Chang and S.-J. Kim, Polymer (Korea) 6 (1), 60 (1982).
C.J. Pedersen and H.K. Frensdorff, Angew. Chem. Int. Ed., 11 (1), 16 (1972).
T.D. N’Guyen and S. Boileau, Polym. Preprints, 23 (1), 154 (1982)
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© 1984 Plenum Press, New York
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Jin, JI., Chang, JH. (1984). Phase-Transfer Polycondensation of Bisphenolate Anions and 1,6-Dibromohexane. In: Mathias, L.J., Carraher, C.E. (eds) Crown Ethers and Phase Transfer Catalysis in Polymer Science. Polymer Science and Technology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9349-2_9
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DOI: https://doi.org/10.1007/978-1-4615-9349-2_9
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