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Basic Behavior of Epoxides in the Presence of Halide Ions
Author(s) -
Buddrus J.
Publication year - 1972
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197210411
Subject(s) - halide , phosphonium , epoxide , chemistry , ion , catalysis , proton , photochemistry , inorganic chemistry , organic chemistry , physics , quantum mechanics
Epoxides behave as bases in the presence of catalytic quantities of halide ions. They convert halogenated hydrocarbons into olefins, suitable phosphonium salts into ylides, and haloforms into dihalocarbenes. Kinetic studies with the aid of JR and NMR spectroscopy show that the species that functions as the proton acceptor is neither the epoxide ion nor the halide ion, but the 2‐haloethoxide ion.