The Reaction of Oxiranes with Carbon Disulfide under High Pressure

• Yoichi Taguchi

  National Chemical Laboratory for Industry

• Koshin Yanagiya

  National Chemical Laboratory for Industry

• Isao Shibuya

  National Chemical Laboratory for Industry

• Yasuo Suhara

  National Chemical Laboratory for Industry

抄録

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 (2b) as the main product and 5-hexyl-1,3-oxathiolane-2-thione (1b) as a minor product. A feasible mechanism for this formation is that 1b and 2-hexylthiirane (4b) are produced in the first stage of reaction, and that 2b is then formed by the reaction of 1b or 4b 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 2b 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 N,N-dimethylethylamine, pyridine, and N-methylmorpholine, serve as good catalysts for the reaction.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 61 (3), 921-925, 1988-03-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360846644033245568
• NII論文ID: 130001981358
• DOI: 10.1246/bcsj.61.921
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/61/3/921/55723516/bcsj.61.921.pdf
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