Cytotoxic compounds. Part XVI. Reactions of the bismethanesulphonates of 3-(N-methylanilino)propane-1,2-diol and of 2-(N-methylanilino)-propane-1,3-diol with nucleophiles

Abstract

The products formed in the reactions of these bismethanesulphonates with various nucleophiles have been identified by n.m.r. spectroscopy. With methanol, both gave only the 1,2-dimethyl ether, but with sodium methoxide identical mixtures of the 1,2- and the 1,3-dimethyl ether were obtained from each. With potassium acetate, both gave identical mixtures of the 1,2- and the 1,3-diacetate. All these reactions proceeded under kinetic control, and the results reflect the variations in the preferred mode of attack on intermediate aziridinium ions. Reactions with sodium phenyl sulphide proceeded partly by direct displacement, not involving a cyclic ion.