2-Substituted Imino-1,3-dithiolanes. Their Thermal Ring-isomerizations and Reactions with Epoxides
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概要
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Thermal ring-isomerization and reactions with epoxides of 2-substituted imino-1,3-dithiolanes (I) were studied. The methylimino (Ia) and ethylimino derivatives (Ib) were found to be ringisomerized to the corresponding 3-alkyl-1,3-thiazolidine-2-thione (V) at about 200°C, while the phenylimino compound (Ic) was not isomerized even under more drastic conditions. The influence of various additives including Lewis acids was also examined. In contrast to the oxygen analog of I, these imino compounds were not polymerized with Lewis acids, and catalysis of any additives on isomerization was not observed. The possibility that I thermally dissociated into methyl isothiocyanate and ethylene sulfide followed by their recombination to V would be excluded by the observation that the reaction of alkyl isothiocyanate with ethylene sulfide at 150°C afforded I in good yield. Reactions of I with epoxides were carried out regarding the isomerization mechanism. All these imino compounds reacted with epoxides to give the 2-oxazolidone derivatives (III) in good yield. Mechanisms of the ring-isomerization and formation of III have been suggested, and the difference in reactivity between I and its oxygen analog has been discussed.
- 公益社団法人 日本化学会の論文
著者
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Okawara Makoto
Research Laboratory Of Resources Utilization Tokyo Institute Of Technology
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Ueno Yoshio
Research Institute For Biosciences And Department Of Toxicology And Microbial Chemistry Faculty Of Pharmaceutical Sciences Science University Of Tokyo
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Nakai Takeshi
Research Laboratory of Resources Utilization, Tokyo Institute of Technology
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Nakai Takeshi
Research Laboratory of Resouces Utilization, Tokyo Institute of Technology
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