102-08-9 Molecular rearrangement of sulfur compounds IX : Pyrolysis of 2-phenylimino-3-arylamino-4-thiazolidinone derivatives

Pyrolysis of 2-phenylimino-3-arylamino-4-thiazolidinone I, II (Ar = Ph, p-tolyl) by heating at ca. 250°C in a sealed tube gives rise to H2S, benzonitrile, acetophenone, arylamines, phenyl isothiocynate, thioglycolic acid, arylhydrazines, N-phenyl-N'-aryl thiourea, benzimidazole, and 3-phenyl-1,2,4-benzotriazines. Analogous results in addition to toluene, bibenzyl, stilbene, bibenzylamine and acetamide were also obtained on pyrolysis of 2-phenylimino-3-benzylamino-4-thiazolidinone (III). In the presence of isoquinoline as a radical trap, (III) gave 1-benzylisoquinoline beside the previous products. A free radical mechanism has been postulated to take place through the homolysis of the N-N and C-S bonds to account for the identified products. https://www.lookchem.com/CASDataBase_102-08-9.htm

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