Skeletal rearrangements through homoenolizable methyl groups in acyclic ketones. The effect of strain on the regioselectivity of β-enolate cleavage

MB Rampersad, JB Stothers

Index: Rampersad,M.B.; Stothers,J.B. Journal of the Chemical Society, Chemical Communications, 1976 , p. 709 - 711

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Abstract

WHILE the generation of enolates by proton abstraction from the /3- and y-carbon atoms of ketones under strongly basic conditions has been examined in a variety of cyclic systems,l relatively little attention has been directed toward acyclic systems, although evidence of the inter- vention of p-enolates in these cases has been established.2 Many of the cyclic systems exhibit skeletal rearrangements through p-enolizable methylene and methine carbon atoms as well as ...