Solvation and catalysis in displacement at phosphorus. Reaction of

J. Org. Chem. 1981, 46, 43-46

43

Solvation and Catalysis in Displacement at Phosphorus. Reaction of Imidazole and Benzoate Ion with p-Nitrophenyl and 2,4-Dinitrophenyl Diphenylphosphinates1f2 Gun Wallerberg and Paul Haake* Department of Chemistry, Wesleyan University, Middletown, Connecticut 06457 Received April 25, 1980

The reactions of two phosphorus esters, p-nitrophenyl diphenylphosphinate (I) and 2,4-dinitrophenyl diphenylphosphinate (11), have been investigated in acetonitrile containing variable amounts of water. The effectivenessof imidazole and benzoate ion as catalysts has been investigated. Whereas the reaction of imidazole with 11 is quite rapid, the reaction with I is very slow. However, I reads predominantly by the rate term k[C&CO