Rearrangement and cleavage of [(aryloxy) methyl] silanes by organolithium reagents: conversion of phenols into benzylic alcohols

JJ Eisch, JE Galle, A Piotrowski…

Index: Eisch, John J.; Galle, James E.; Piotrowski, Andrzej; Tsai, Miin-Rong Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5051 - 5056

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Citation Number: 21

Abstract

Results Synthesis of [(Aryloxy) methyl] silanes. The [(ary1oxy) methyll trimethylsilanes (3) were prepared from the corresponding phenols (6) in high yields by two different procedures:(a) the preparation of the sodium phenoxide from sodium hydride in dimethyl sulfoxide and subsequent heating with (chloromethy1) trimethylsilane (7)[or with (chloromethy1) triphenylsilane (S)] or (b) the concerted interaction of the phenol 6, 7, and ...