The 9-decalyl and related cations. VI. Solvolysis of Pent-4-enyl p-nitrobenzenesulfonate in 1,1,1,3,3,3-Hexafluoropropan-2-ol and of 3-(Cyclohex-1'-enyl)propyl p-Nitrobenzenesulfonate in 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoropropan-2-ol

Abstract

Kinetic and product studies have established that pent-4-enyl p-nitrobenzenesulfonate undergoes insignificant solvolysis (1.5 %) by the π-route in 1,1,1,3,3,3-hexafluoropropan-2-ol.

π-Participation to give the perhydroinden-3a-yl (8-hydrindyl) cation during the solvolysis of 3-(cyclohex-1'-enyl)propylp-nitrobenzenesulfonate, a substituted pent-4-enyl derivative, in fluorinated alcohols is, however, significant. In buffered 2,2,2-trifluoroethanol, it occurs to the extent of 30%; in buffered and unbuffered 1,1,1,3,3,3-hexafluoropropan-2-ol, the values are 96 and 98 %, respectively.