Allylic carbonium ions. Part I. Acetolysis of 1,1- and 3,3-dimethylallyl 2,4-dinitrophenyl ether

Abstract

The 2,4-dinitrophenyl ethers of 1,1- and 3,3-dimethylallyl alcohol were prepared by convenient new arylation techniques, and their acetolysis rates and reaction products are reported. The tertiary isomer undergoes concurrent rearrangement to the primary isomer by a process of ion-pair return. Experiments relating these solvolyses to similar processes already described, involving other leaving groups and solvents, are reported.