Journal of Organic Chemistry p. 1328 - 1334 (1990)
Update date:2022-08-05
Topics:
Bates, Robert B.
Siahaan, Teruna J.
Suvannachut, Kessara
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 45-80percent yields.Rearrangement products are obtained in 10-30percent 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 recombination of the resulting radical pair in a different way.The rearrangements can be avoided by using methyl ethers and working at or below room temperature.
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