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The Generation of the Diisopropyl Nitroxide Radical During the Reaction of Lithium Diisopropylamide With α-Fluoroacetate Esters

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The formation of an EPR active species was observed when lithium diisopropylamide (LDA) was employed as the base for deprotonation of fluoroacetates. The EPR of a glass prepared from the reaction mixture showed an intense signal. The solution EPR spectrum of the sample was independent of temperature, and exhibited a hyperfine structure which allowed identification of the radical species as diisopropyl nitroxide. Generation of the enolate by metalation of ethyl fluoroiodoacetate gave no evidence for autoxidation occurring in the absence of diisopropylamine.

Affiliations: 1: Department of Chemistry, State University of New York at Albany, Albany, New York 12222 U.S.A


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