Journal of the Chemical Society, Perkin Transactions 2

Cascade rearrangement of spiroepoxymethyl radicals into 2-oxocycloalkyl radicals: evaluation of a two-carbon cycloalkanone ring expansion

JC Walton

Index: Afzal, Mohammad; Walton, John C. Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 5 p. 937 - 945

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Citation Number: 5

Abstract

Series of 2-bromomethyl-and 2-hydroxymethyl-1-oxaspiro [2. n] alkanes were prepared from cycloalkanones by initial Wadsworth–Horner–Emmons methodology to afford ester- substituted methylenecycloalkanes. The latter were selectively reduced to hydroxymethylmethylenecycloalkanes which were epoxidised with peroxyacetic acid. Homolytic reactions were studied by EPR spectroscopy which enabled transient 3-oxoalk- ...