The reaction of oxiranes with carbon disulfide under high pressure.

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概要

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• The reaction of 2,2-dimetyloxirane with carbon disulfide in the presence of triethylamine was accelerated under high pressure to give 5,5-dimethyl-1,3-oxathiolane-2-thione in a high yield, while 2-hexyloxirane under the same reaction condition formeds 4-hexyl-1,3-dithiolane-2-thione (<B>2b</B>) as the main product and 5-hexyl-1,3-oxathiolane-2-thione (<B>1b</B>) as a minor product. A feasible mechanism for this formation is that <B>1b</B> and 2-hexylthiirane (<B>4b</B>) are produced in the first stage of reaction, and that <B>2b</B> is then formed by the reaction of <B>1b</B> or <B>4b</B> with carbon disulfide. In reactions of a variety of oxiranes with carbon disulfide, 1,3-dithiolane-2-thiones were obtained in high yields under 800 MPa at 100 °C within 20 h. Concerning the effect of substituents in oxiranes, the selectivity for product <B>2b</B> is in the decreasing order; 2-phenyl->2-methyl->2-ethyl->2-hexyl->2,3-tetramethylene->2,2-dimethyl->2-(chloromethyl)-. Tertiary amines, such as <I>N</I>,<I>N</I>-dimethylethylamine, pyridine, and <I>N</I>-methylmorpholine, serve as good catalysts for the reaction.

• 公益社団法人 日本化学会の論文

著者

• TAGUCHI Yoichi

  National Institute of Advanced Industrial Science and Technology (AIST)

• SUHARA Yasuo

  National Chemical Laboratory for Industry

• Shibuya Isao

  National Chemical Laboratory for Industry

• Yanagiya Koshin

  National Chemical Laboratory for Industry

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