Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 14: Regioselectivity of the opening reactions with MeOH of remote O-substituted 1,2-epoxycyclohexanes under gas-phase operating conditions

摘要

The regiochemical behavior of cyclohexene oxides bearing a remote O-functionality was determined in the gas-phase in opening reactions with MeOH, using a gaseous acid (D-3(+), CnH5+, Me2F+) as the promoting agent. The results obtained indicate the incursion in the opening process in the gas phase of H+ (or D+)-mediated chelated bidentate species completely absent in the corresponding reactions (methanolysis) carried out in the condensed phase. (C) 2000 Elsevier Science Ltd. All rights reserved. [References: 23]