Electrophilic substitution at phosphorus: reactions of diphenylphosphinyl systems with carbonyl compounds
Abstract
Methods of making adducts of diphenylphosphine oxide include the addition of its anion, either as a Grignard reagent or as the sodium salt, to carbonyl compounds. With acetone, the Grignard method gave a substantial yield of a phorone (2,6-dimethylhepta-2,5-dien-4-one) bis-adduct, and with enones addition occurred either to the carbonyl group or to the double bond. A new reaction is described in which a nucleophilic Ph2PO group is released, by the debenzylation and decarboxylation of benzyl diphenylphosphinylformate, to react with carbonyl compounds or iodine. The debenzylation can be separated kinetically from the rest of the reaction.