Skeletal rearrangements through homoenolizable methyl groups in acyclic ketones. The effect of strain on the regioselectivity of β-enolate cleavage
Abstract
Di-t-butyl ketone and 5,5,7,7-tetramethylunde-can-6-one have been found to isomerize slowly under strongly basic conditions (ButO––ButOH, 185 °C), constituting the first examples of skeletal rearrangement through β-enolizable (homoenolizable) methyl groups.