Meta substitution in electrophilic benzylations of 2, 6-dimethylphenol and alkyl 2, 6-dimethylphenyl ethers: product distributions and mechanism

…, MP McLaughlin, VC Marhevka

Index: Miller, Bernard; McLaughlin, Michael P.; Marhevka, Virginia C. Journal of Organic Chemistry, 1982 , vol. 47, # 4 p. 710 - 719

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Citation Number: 10

Abstract

Electrophilic benzylations of 2, 6-dimethylphenol and 2, 6-dimethylanisole under a variety of conditions yield ca. 40% and 70%, respectively, of the meta substitution products, although other electrophilic substitution reactions appear to proceed exclusively at the para positions. Similar results were obtained with other alkyl 2, 8dimethylphenyl ethers and with 2, 6- diallylanisole. A variety of possible mechanisms were investigated and shown to be ...