The Journal of Organic Chemistry

(E)-3-(Trimethylsilyl)-2-propen-1-ol. An improved preparation

SE Denmark, TK Jones

Index: Denmark, S. E.; Jones, T. K. Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4595 - 4597

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Citation Number: 184

Abstract

RCN t Bu2SnS (2) involves nucleophilic attack by sulfur on the Sn= O function to give reactive intermediate 1, where X= H. It is known, however, that dibutyltin oxide and methanol rapidly forms dibuty1dimetho~ ytin. l~ It is therefore probable that attack by sulfur at the tin atom also involves this dimethoxytin derivative to give intermediate 1, where X= Me. Either form of 1 can undergo a/3 elimination (presumably by the El mechanism illustrated) to ...