Solvolysis of 1-aryl-2,2,2-trihalogenoethyl toluene-p-sulphonates. Generation of carbocations destabilized by trichloro- or tribromo-methyl groups
Abstract
The kinetics of solvolysis of the title compounds, leading to the formation of carbocations destabilized by a CCl3 or a CBr3 group, have been studied in various solvents. Destabilization by the CX3 group increases with the electronegativity of the halogen X. Plots of log k vs. YOTs, for the 1-(p-methoxyphenyl)-2,2,2-trihalogenoethyl p-toluenesulphonates yield mOTs values which are indicative of some deviation from a pure kc process, probably due to anchimeric assistance by the halogen substituents.