The Journal of Organic Chemistry

Selenium stabilized anions. Selenoxide syn elimination and sila-Pummerer rearrangement of. alpha.-silyl selenoxides

HJ Reich, SK Shah

Index: Reich,H.J.; Shah,S.K. Journal of Organic Chemistry, 1977 , vol. 42, # 10 p. 1773 - 1776

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Citation Number: 49

Abstract

Several a-silyl selenides (2, 10) have been prepared by silylation of a-lithio selenides and alkylation of a-lithioa-silyl selenides. Oxidation of these selenides to selenoxides results in competitive selenoxide syn elimination to give vinyl silanes (4) and sila-Pummerer rearrangement to give vinyl selenides (8) and carbonyl compounds. The ratio can be controlled to some extent by control of reaction conditions, but a more pronounced change ...