Regioselective Alkylation of Anthrahydroquinone and Anthrone in Water with Quinonemethides and Other Alkylating Agents

Article abstract of DOI:10.1021/jo00340a006

Antrahydroquinone (AHQ) and anthrone are alkylated in the C10 position by quinonemethides, generated in situ from p-acetoxybenzyl chlorides, to give adducts 13-15, 24, 25, 28, 29, and 32.Aqueous alkylations of AHQ with methyl vinyl ketone, cinnamaldehyde, and benzyl chloride also produces C10-substituted 10-hydroxyanthrones.Simple ketones and aldehydes do not, however, alkylate AHQ in aqueous alkali.