Regiochemical control of the ring opening of aziridines by means of chelating processes. Part 3: Regioselectivity of the opening reactions with methanol of remote O-substituted regio- and diastereoisomeric activated aziridines under condensed- and gas-phase operating conditions

Abstract

The regiochemical behavior of the pairs of diastereoisomeric activated aziridines 1– 8 deriving from the cyclohexane system, bearing a remote O-functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D 3 +) as the promoting agent. The results obtained in the opening process of the cis diastereoisomers indicate the constant incursion in the gas phase of D +(corresponding to H +)-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in the cd-phase.