Abstract
Oxidative fragmentation of γ-trimethylsilyl alcohols with cerium ammonium nitrate occurs rapidly via a radical process to provide keto olefins. Attempts to obtain the same products via an ionic-type 1,4-elimination with the trimethylsilyl group as the directing moiety proved unsuccessful, even under a variety of harsh experimental conditions. Instead, dehydration products were produced in certain cases. © 1987.