Alkylation of quinones by carbanions: use of pyridinium ylides to insert phenacyl, acetonyl and related groups

Abstract

Reports that carbanions C^– add to quinones Q in the ratios 1:1 and 2:1 are confirmed; even if an excess of quinone is present, cage or bridge products are formed only if the carbanion is itself quinonoid. Pyridinium salts C₅H₅[graphic omitted]CH₂COR X^– react with quinones in mildly basic solvents to give acetonylquinones and other quinones containing the group RCOCH₂.