Tetrahedron

Novel free radical ring-expansion reactions

P Dowd, SC Choi

Index: Dowd, Paul; Choi, Soo-Chang Tetrahedron, 1989 , vol. 45, # 1 p. 77 - 90

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Citation Number: 121

Abstract

A novel free radical initiated ring expansion of haloalkyl β-keto esters is described. Following alkylation of the β-keto ester with the appropriate dihalide, the resulting halide is treated at reflux with tri-n-butyltin hydride. Rearrangement to the homologated γ-keto ester occurs smoothly. An oxy radical intermediate is proposed for the reaction.