The synthesis of 1,3-dithiolan-2-ones on the reaction of oxiranes with carbon disulfide under high pressure.

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概要

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• An equimolar reaction of 2-hexyloxirane with carbon disulfide in hexane was run in the presence of triethylamine under 800 MPa at 100 °C for 20 h, and gave 63% of 4-hexyl-1,3-dithiolan-2-one (<B>3a</B>), 21% of 4-hexyl-1,3-dithiolane-2-thione (<B>1a</B>) and 5% of 5-hexyl-1,3-oxathiolan-2-one (<B>4a</B>). Hexane, benzene, and diisopropyl ether were good solvents for the reaction. The reaction of a variety of oxiranes with carbon disulfide produced 1,3-dithiolan-2-ones as the main products under 500 MPa at 100 °C for 20 h. Upon a reaction of 2-hexyloxirane with carbon disulfide, 5-hexyl-1,3-oxathiolane-2-thione (<B>2a</B>), and 2-hexylthiirane (<B>5a</B>) were produced during the first stage of reaction. The formation of <B>1a</B> and <B>4a</B> began immediately, whereas, the formation of <B>3a</B> required a long induced period. A feasible mechanism for the formation of <B>3a</B> is proposed to be a rearrangement of <B>2a</B> in the presence of triethylamine, free from carbon disulfide.

• 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)

• YASUMOTO Masahiko

  National Chemical Laboratory for Industry

• SUHARA Yasuo

  National Chemical Laboratory for Industry

• Shibuya Isao

  National Chemical Laboratory for Industry

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