Carbonyl Homologation via β-Trimethylsilyl β-Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction

T. Howard Black Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920

Yong Zhang Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920

Jianhua Huang Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920

Douglas C. Smith Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920

Bryan E. Yates Department of Chemistry, Eastern Illinois University, Charleston, Illinois, 61920

Abstract

Saturated and unsaturated aldehydes and ketones, when treated with trimethylsilylketene and BF₃ for 16 hours, form β-lactones which spontaneously rearrange to α,β-unsaturated TMS esters; these hydrolyze during workup to form the corresponding carboxylic acids.

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Carbonyl Homologation via β-Trimethylsilyl β-Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction

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Carbonyl Homologation via β-Trimethylsilyl β-Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction

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