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Electrochemically induced transformation of 4-halomethyl-4-methylcyclohexa-2,5-dien-1-ones into 3,4-dimethylphenol
Authors:G V Gavrilova  A A Moiseeva  E K Beloglazkina  A A Gavrilov  N V Zyk
Institution:(1) Faculty of Chemistry, Moscow State University, Vorob’evy gory 1, Moscow, 119992, Russia
Abstract:Electrochemical behavior of 4-halomethyl-4-methylcyclohexa-2,5-dien-1-ones and 2,6-dibromo-4,4-dimethylcyclohexa-2,5-dien-1-one was studied. Reductive dehalogenation of cyclohexa-2,5-dien-1-ones having a halogen atom at the neopentyl-like carbon atom gives the corresponding carbanion which undergoes anionic cyclopropyl-allyl rearrangement with subsequent addition of proton to form 3,4-dimethylphenol.
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