Theoretical and Experimental Studies on the Regioselectivity of Epoxide Ring Opening by Nucleophiles in Nitromethane without any Catalyst: Nucleophilic-Chain Attack Mechanism

Abstract

We describe here a mild and efficient method for the nucleophilic ring-opening of epoxides with amines, alcohols and water in the presence of nitromethane as a polar solvent without using any catalyst. The reactions are highly regioselective and afford the products in excellent yields within a short period of time at room temperature. The regioselectivity for this ring opening has been investigated using experimental and theoretical 1H and 13C NMR studies together with activation energy calculations at the B3LYP/6-311+G(2d,p) level of theory. The mechanism of nucleophilic attack has been investigated in terms of a direct attack or a methanol chain attack.