SN2 CHARACTER OF SOLVOLYSES OF TERT-BUTYL HALIDES AND OF TRIFLUOROACETOLYSES OF SECONDARY ALKYL SULFONATES

The importance of nucleophilic solvent assistance1is now well established for many solvolyses, e.g., simple secondary alkyl sulfonates2-6and β-aryl systems.7We now report evidence for two additional, important, and unexpected cases of significant nucleophilic solvent assistance: (1) solvolyses of ten-butyl halides, key reference points for structural8and medium effects9on the reactivity of organic systems; (2) trifluoroacetolyses of simple secondary alkyl sulfonates, previously assumed to be SN1 (limiting) reactions and used as reference points for minimum estimates of nucleophilic solvent assistance in more nucleophilic media.2,4,10. © 1979, American Chemical Society. All rights reserved.