Abstract
The epimeric dl-1-phenyl-2-aminopropanethiols (threo-XI and erythro-XI), corresponding to thiol derivatives of norephedrine, were synthesized by various routes and their configurations were assigned from their formation mechanism and chemical properties. The substance of C10H11ONS, formed by the action of carbon disulfide and potassium hydroxide on epimeric dl-1-phenyl-2-aminopropanols (threo-I and erythro-I), was found from infrared spectra and reaction routes to be the epimeric dl-4-methyl-5-phenyloxazolidine-2-thione, with no change in the steric configuration, and not the epimeric dl-4-methyl-5-phenylthiazolidine-2-one (threo-XIV and erythro-XIV) obtained by one inversion.
