Reactions of 2-chloroacyltrimethylsilanes with Grignard reagents. Preparation of 3-(trimethylsilyl)-2-alkanones and 2-(trimethylsilyl)-1-alkanols

T Sato, K Matsumoto, T Abe, I Kuwajima

Index: Sato, Toshio; Matsumoto, Kazuhisa; Abe, Toru; Kuwajima, Isao Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 8 p. 2167 - 2170

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Citation Number: 9

Abstract

Reactions of 2-chloroacyltrimethylsilanes with Grignard reagents have been examined. Thus, treatment with methylmagnesium iodide affords the corresponding 3-(trimethylsilyl)-2- alkanones through an initial addition followed by removal of chloride anion and 1, 2- rearrangement of silyl group. In contrast, the reaction proceeds with 2 equiv of the Grignard reagents bearing β-hydrogen to give 2-(trimethylsilyl)-1-alkanols, where initial reduction of ...