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Organic Chemistry

Phase Transfer Catalysis; Nucleophilic Substitution of β-Bromohydrins with Anions in Solid-Liquid System

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Pages 2169-2172 | Received 04 Jun 1979, Published online: 09 Sep 2014

References

  • W. P. Weber and G. W. Gokel, “Phase Transfer Catalysis in Organic Synthesis,” Springer Verlag, Berlin, 1977; C. M. Starks and C. Liotta, “Phase Transfer Catalysis,” Academic Press Inc., New York, N. Y., 1978.
  • Y. Nakajima, R. Kinishi, J. Oda, and Y. Inouye, Bull. Chem. Soc. Japan, 50, 2025 (1977); Y. Nakajima, J. Oda, and Y. Inouye, Tetrahedron Lett., 3107 (1978).
  • H. Normant, T. Cuvingny, and P. Savignac, Synthesis, 805 (1975).
  • These results may possibly be related to an equilibrium between 9 and 10 involving acyl migration. However, this possibility can be excluded by the experimental fact that the rearrangement product 10 was not detected at all, when 9 was subjected to the same treatment as was employed for the reaction.
  • N. Watanabe, M. Okano, and S. Uemura, Bull. Chem. Soc. Japan, 47, 2745 (1974).
  • J. M. Stewart, J. Org. Chem., 28, 596 (1963).
  • W. L. F. Armarego, “Stereochemistry of Heterocyclic Compounds,” Wiley Interscience, New York, 1977, Part 2, p. 172 ff.

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