Solvolysis rate constants in MeOH and t‐BuOh are compared for β‐methyl and β‐phenyl derivatives of two cycloakyl systems. It appears that the β‐phenyl derivatives solvolyse at te 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 phelyl or by the solvent. A parallel between phenyl assistance and ‘SN2 (intermediate)’ mechanism, suggested by Bentely & Schleyer, is drawn.