Abstract

Upon heating, 3-methylene-1,4-cyclohexadienes possessing an alkoxycarbonyl substituent in position 6 undergo rearrangement and concomitant aromatization to give the corresponding arylacetates. This transformation represents a modification of the von Auwers rearrangement and proceeds by a radical chain mechanism. The intermediate alkoxycarbonyl radical can be intercepted allowing further useful synthetic variations.

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