The Preparation of Methyl (E)- and (Z)-O-Methylbenzothiohydroximates

Abstract

A series of methyl (Z)-O-methylbenzothiohydroximates were prepared either by reaction of the corresponding (Z)-N-methoxybenzenecarboximidoyl bromides with potassium fluoride in dimethyl sulfoxide, or by reaction of N-methoxybenzamides with Lawesson’s reagent followed by alkylation. Irradiation of the Z isomers led to a photostationary equilibrium containing mixtures of approx. 40% E and 60% Z, from which the E isomers were isolated.