Abstract:
Systematic variation of the ratio of Hünig's base 1 to S2Cl2 in their reactions in chloroform shows that, in addition to known tricyclic bisdithiolothiazine thiones 4 and 5, monocyclic dithiole-3-thiones 6 and 7 can be isolated; when the inert base DABCO is added the extent of sulfuration of the products is reduced and thiones are replaced by their oxo analogues, and diisopropylamines 15 are converted into monocyclic dithiol-3-ones 16; an overall mechanistic rationalisation of the results, extending earlier work, is presented.