Effects of Nonionic Micelles on the Rate of Mononuclear Heterocyclic Rearrangement of (Z)-Phenylhydrazones of 5-Substituted 3-Benzoyl-1,2,4-oxadiazoles.
Nonionic Triton X-100 micelles solubilize the otherwise water-insoluble (Z)-phenylhydrazones of some 5-substituted 3-benzoyl-1,2,4-oxadiazoles to an extent suitable for studying the occurrence of a general-base-catalyzed rearrangement in the presence of borate buffers (pH 9.6). The kinetic data, obtained at 40.0 degrees C over a wide range of surfactant concentrations, are found to conform to a reaction scheme which implies partitioning of the substrates and the base between water and the micellar pseudophase. Evidence that both the rate of the rearrangement reactions and the binding of the substrates to the micellar aggregates are primarily governed by the steric requirements of the 5-substituent group is obtained. Copyright 2001 Academic Press.
Guernelli
Susanna
S
Dipartimento di Chimica Organica "E. Paternó", Viale delle Scienze, Palermo, 90128, Italy
Noto
Renato
R
Sbriziolo
Carmelo
C
Spinelli
Domenico
D
Liveri
Maria Liria Turco
ML