15571-99-0Relevant articles and documents
AMINOLYSIS OF MONOPHENYL SUCCINATES IN APROTIC SOLVENTS. PART I. CYCLIZATION OF MONOPHENYL SUCCINATES TO SUCCINIC ANHYDRIDE
Bartnicka, H.,Smagowski, H.
, p. 1277 - 1286 (2007/10/02)
The reaction of benzylamine with monophenyl succinates in aprotic solvents has been shown to proceed simultaneously in two directions.A one-step (bimolecular) pathway involved internal and external catalysis, whereas a two-step pathway involved preliminary cyclization of the monoester to succinic anhydride followed by benzylaminolysis of the latter.In an effort to establish factors contributing to either of the two pathways of benzylaminolysis of the monoesters, a kinetic study of individual reactions has been undertaken.The cyclization of the monophenyl succinateswas studied in dioxane, benzene, N,N-dimethylformamide, pyridine and a pyridine-acetonitrile mixture.The rate of cyclization was proportional to the basicity and the electric permittivity of solvent, electron-accepting capacity of the substituent in the phenyl group of the monoester and inversely proportional to the initial concentration of the monoester.The mechanism of cyclization of the monoesters has been discussed.
