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 1 H and 13 C 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.
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