Journal of the American Chemical Society

New anionic rearrangements. XVII. 1, 2-Anionic rearrangements from oxygen to carbon in benzyloxyorganosilanes and benzyloxyorganogermanes

A Wright, R West

Index: Wright,A.; West,R. Journal of the American Chemical Society, 1974 , vol. 96, # 10 p. 3214 - 3222

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Citation Number: 88

Abstract

Abstract: Benzyloxytrimethylsilane (la), benzyloxytrimethylgermane (lh), trimethylgermyloxydiphenylmethane (lj), and various related compounds, upon metalation at the benzyl carbon atom with excess tert-butyllithium or Lithium diisopropylamide in tetrahydrofuran, rearrange rapidly via a 1, 2-shift of silicon or germanium to the a carbanion to give, in high yield, anions of a-hydroxy-a-trimethylsilyltoluene (Za), a-hydroxy-a- ...