The reaction of N-methylbenzothiazole-2-selone and 1,1-dimethylselenourea with sulfuryl chloride and dichlorine†

Abstract

The reactions of N-methylbenzothiazole-2-selone, mbts, and 1,1-dimethylselenourea, dmsu, with dichlorine and the chlorinating agent SO₂Cl₂ have been investigated. In the 1∶1 reactions spectroscopic evidence for the formation of 1∶1 selenoamide·Cl₂ adducts was obtained; unfortunately, crystallisation attempts have so far been unsuccessful. A single crystal X-ray diffraction was performed, however, on an ionic minor product from the reaction of mbts with one equivalent of SO₂Cl₂. When two equivalents of SO₂Cl₂ or an excess of dichlorine gas were treated with mbts or dmsu a variety of ionic products were obtained, the exact nature of which varied depending upon which chlorinating agent is used, the identity of the selenoamide and the stoichiometry of the reactants. The reactions are therefore complicated and, in most cases, several products are obtained from a given reaction. This study represents the first reported reactions of selenoamides with chlorinating agents and two new selenium–chlorine binary anions have been crystallographically characterised for the first time, namely Se₂Cl₄^2– and SeCl₆^2–.