Helvetica Chimica Acta p. 352 - 360 (1984)
Update date:2022-08-11
Topics:
Laureillard, Jeanne
Casadevall, Andre
Casadevall, Eliette
Solvolysis rate constants in MeOH and t-BuOH are compared for β-methyl and β-phenyl derivatives of two cycloalkyl systems.It appears that the β-phenyl derivatives solvolyse at the same rate as the β-methyl ones.The lack of deceleration is attributed to phenyl assistance.It is established by configurational analysis of the reaction products, that those products which necessarily originate from a cationic species are the most abundant ones.It is suggested that these reactions could proceed through ion-pair intermediates, which are nucleophilically solvated by phenyl or by the solvent.A parallel between phenyl assistance and 'SN2 (intermediate)' mechanism, suggested by Bentley and Schleyer, is drawn.
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