Richard L. Wife

ADDITION OF DIPHENYLPHOSPHINE TO MALEIC ANHYDRIDE AND RELATED COMPOUNDS

Abstract A Michael addition of secondary phosphines to activated olefins containing the ethenedione moiety such as maleic anhydride, maleic ester and dibenzoylethene leads to functionalised tertiary phosphines. Reactions of activated olefins which contain a carboxylic group do not lead to the expected adducts; instead, phosphonium salts are formed by a sequence of reactions. A hydrogen shift plays a crucial role both in the reaction that leads to the adduct and in the reaction that leads to the phosphonium salt. Phosphinosuccinic anhydrides and phosphinosuccinic esters can be transformed into the corresponding succinic acids. Decarboxylation of phosphinosuccinic acids leads to phosphinopropionic acids.