Aziridine formation by reduction of ketoximes with lithium aluminium hydride: On dibenzylketoxime and its o-substituted derivatives

K Kotera, Y Matsukawa, H Takahashi, T Okada…

Index: Kotera,K. et al. Tetrahedron, 1968 , vol. 24, p. 6177 - 6184

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Citation Number: 13

Abstract

The reduction of dibenzylketoxime (Ia) with LAH in boiling THF gave cis-2-phenyl-3-benzyl- aziridine (IIa) in excellent yield, together with a small amount of the expected primary amine, 2-amino-1, 3-diphenylpropane (III). The LAD reduction of Ia was carried out and the position of deuterium introduced was based on the NMR data. The O-substituted derivatives of Ia, such as O-Me, O-acetyl and O-tosyl derivatives (Ib, Ic and ID), were also reduced with LAH ...