Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 18: Regioselectivity of the opening reactions with MeOH of 1-(benzyloxy)-2,3- and -3,4-epoxyalkanes under condensed and gas phase operating conditions

The regiochemical behavior of a series of aliphatic open chain epoxides bearing a heterofunctionality in an allylic or homoallylic relationship has been examined in the opening reaction with MeOH under both condensed and gas phase operating conditions. The results indicate that the proton (actually D+) possesses in the gas phase intrinsic chelating properties which are even superior than those of Li+ in the condensed phase.