Journal of Organic Chemistry p. 1904 - 1909 (1982)
Update date:2022-08-03
Topics:
Davidson, Robert I.
Kropp, Paul J.
Oxidation of a series of alkyl halides with alcoholic 3-chloroperoxybenzoic acid afforded the results outlined in Charts I-III and Tables I-III.The reaction was found to be a powerful and convenient method for effecting nucleophilic substitution in a variety of systems, including the highly inert 1- and 7-bicyclo<2.2.1>heptyl systems.Qualitatively, the number of molar equivalents of oxidant required varied inversely with the expected ease of substitution for a given system.A mechanism is suggested whereby the iodide is oxidized stepwise to a species RIOn in which n is an integer sufficiently large that the system in question will undergo nucleophilic substitution or elimination.Reaction in the presence of added chloride or bromide ion usually resulted in a facilitation of reaction rate and a decrease in the number of molar equivalents of oxidant required; the principal product under these conditions was usually the corresponding chloride or bromide.
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