Cycloaddition Elimination Reactions of Phenylisocyanate with Oxo and Thiono Derivatives of Aliphatic Substituted 5-Imino-1,2,4-dithiazolidines and 3-Thiono-1,2,4-thiadiazolidines (Mustard Oil Oxides and Sulfides))

Article abstract of DOI:10.1002/prac.19923340808

5-Imino-1,2,4-dithiazolidin-3-ones 1 and -3-thiones 3 react with phenylisocyanate to afford 5-imino-1,2,4-thiadiazolidin-3-ones 6.In comparison isomeric 3-thiono-1,2,4-thiadiazolidin-5-ones 2, 5, and -5-thiones 4 yield 3-imino-1,2,4-thiadiazolidin-5-ones 8, 10, and -5-thiones 7.Thermolyses of thiadiazolidines 5 and 10 afford further 1,2,4-thiadiazolidines 9, 11.Compounds 8-11 are available also by reaction of substituted guanidines with chlorocarbonyl sulfenylchloride.