Investigation of 1,4-elimination reactions of γ-trimethylsilyl alcohols via ionic and radical processes

Article abstract of DOI:10.1016/0022-328X(87)85122-7

Oxidative fragmentation of γ-trimethylsilyl alcohols with cerium ammonium nitrate occurs rapidly via a radical processes 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 unsuccesful, even under a variety of harsh experimental conditions.Instead, dehydration products were produced in certain cases.