The Formation and Chemical Properties of Diastereomeric 1, 2-Dimethyl-3-phenylaziridine

Abstract

L-threo-1, 2-Dimethyl-3-phenylaziridine (threo-III) was, for the first time, isolated in the form of picrate either partly by action of KOH on the supposed L (+)-⩛-ephedrine O-sulfate (threo-V) or wholly by action of NaOH on L (+)-threo-1-chloro-1-phenyl-2-methylamino-propane (threo-II). These observations revised the previous claim that the reaction in the latter case would not initially pass into the aziridine, but into others, e.g. β-methylstyrene derivative, which could not be identified because it polymerized rapidly. The aziridine polymerizes very easily in the free state and more or less easily even in the salt form. It was also discussed that the steric requirement for the aziridine formation favored L-threo-aziridine more than the L-erythro-diastereomer in the transition state of the reaction. The conclusion was supported by the formation ratio of both aziridines roughly calculated on the ground of optical rotatory power.