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Substitution Reactions on Iodine and Bromine: Mechanisms for Facile Halogenations of Heterocycles

Author:
Donham, Leah L., Gronert, Scott
Source:
Journal of organic chemistry 2019 v.84 no.9 pp. 5757-5762
ISSN:
1520-6904
Subject:
bromine, chemical reactions, chemical structure, gases, iodine, organic chemistry, perfluorocarbons
Abstract:
Gas-phase techniques were used to examine the halogenation of deprotonated heterocycles by perfluoroaryl and perfluoroalkyl halides. The results indicate that SN2@Br and SN2@I reactions can be very facile and are effective means of halogenating heterocycles. 2-Iodoheptafluoropropane is exceptionally selective for SN2@I reactions with yields upward of 90%. The results also provide evidence counter to the recent suggestion that t-butoxide-induced halogenations of heterocycles proceed via a radical mechanism.
Agid:
6397530