The reaction of 2,2-dimethylthiirane with carbon disulfide in the presence of triethylamine was accelerated under high pressure to give 4,4-dimethyl-1,3-dithiolane-2-thione nearly quantitatively. The activation volume of this reaction at 40 °C was estimated to be −41 ml mol−1. The rate of the reaction was proportional to the amount of triethylamine when a limited amount of triethylamine was used. The reaction of 2-methylthiirane, 2-hexylthiirane, 1,2-epithiocyclohexane, and 2-phenylthiirane with carbon disulfide gave the corresponding 1,3-dithiolane-2-thione derivatives in good yields. 2-Chloromethylthiirane was less reactive to carbon disulfide than other thiiranes under high pressure. Tertiary amines such as N,N-dimethylethylamine, pyridine, and N-methylmorpholine were good catalysts of the reaction.

中文翻译：

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1,3-二硫戊环-2-硫酮衍生物的合成

在三乙胺的存在下，2,2-二甲基硫杂环丙烷与二硫化碳的反应在高压下加速，得到几乎定量的4,4-二甲基-1,3-二硫杂环戊烷-2-硫酮。该反应在 40 °C 下的活化体积估计为 -41 ml mol-1。当使用有限量的三乙胺时，反应速率与三乙胺的量成正比。2-甲基硫杂环丁烷、2-己基硫杂环己烷、1,2-环硫杂环己烷和2-苯基硫杂环己烷与二硫化碳的反应以良好的产率得到相应的1,3-二硫杂环戊烷-2-硫酮衍生物。2-氯甲基硫杂丙环在高压下对二硫化碳的反应性低于其他硫杂丙环。N,N-二甲基乙胺、吡啶和N-甲基吗啉等叔胺是该反应的良好催化剂。