Selected chemistry of sulfur-containing compounds : thiones, [beta]-thiolactones, and carboxylic-sulfinic acid anhydrides

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1979
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Three types of reactions have been detected for thiocarbonyl- Containing compounds with diphenyl ketene (17). An unusual S -> O replacement reaction has been observed for a series of thiones. Treatment of N-methyl-N1-acetyl (9a) and N-methyl-N'-carbomethoxy (9b) imidazolidinethione with 17 gave the corresponding imidazolIdone IOa and 10b, respectively, A similar process was noted for the reaction of N-methyl-N1-carbomethoxybenzimidazole-2-thione (29a) and N-methylbenzo- thiazole-2-thione (30a) with 17. However, treatment of N-H substituted thiones [N-acetylimidazolidinethione (9c), N-Carbomethoxyimidazolidine- thione (9d), 2-mercaptobenzimidazole (34a), 2-mercaptobenzothiazole (35a), and N-methyl-2-mercaptobenzimidazole (36a)] with 17 led to the formation of 4:1, 2:1, and 1:1 adducts. In these cases, reaction occurred at the nitrogen site. Finally, addition of U, to either ethylene trithiocarbonate (43a) or N,N-dimethylthioformamide (44a) gave the corresponding alkenes 45 and 46 along with carbon oxysulfide. [...]

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