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■ Remarkably Easy Oxidation of Alkylzinc Reagents in Their Reactions with Electrophiles to Produce Alkoxylated Instead of the Expected Alkylated Products

Alan R. Katritzky* and Zhushou Luo

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.

Abstract

Alkylzinc reagents, in contrast to arylzinc reagents, react with two series of α-benzotriazolylalkylamines to give oxidized products formed by the incorporation of an atom of oxygen into the carbon-zinc bond even when the reactions are carried out under argon. Thus, benzotriazole derivatives of 4,5-disubstituted imidazolidinone (2) and N-Boc-2-benzotriazolylpyrrolidine (7) gave oxidized products (4a-b) and (8a-c), respectively. The abnormal reaction course was traced to molecular oxygen dissolved in the THF. The expected, unoxidized products (9a-d) were obtained under rigorous argon purge of the THF solvent and solutions.