A new rearrangement of alkoxybenzyl anions

…, TJ Siahaan, K Suvannachut

Index: Bates, Robert B.; Siahaan, Teruna J.; Suvannachut, Kessara Journal of Organic Chemistry, 1990 , vol. 55, # 4 p. 1328 - 1334

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Citation Number: 15

Abstract

Alkyl groups migrate from oxygen to carbon in alkyl aryl ethers which have been metalated in benzylic positions. 2, 6-Dimethylanisole provides a variety of 2, 6-dialkylphenols and their ethers in 45-80% yields. Rearrangement products are obtained in 10-30% yields from other dimethylanisoles and from methylanisoles. The reactions appear to proceed, like Wittig rearrangements, by homolytic cleavage of the alkyl-oxygen bond followed by ...

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