Preparation of a new 1,2,3-trithiolane, trans-9,10,11-trithiabicyclo[6.3.0]undecane, and its oxidation reactions |
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Authors: | Akihiko Ishii Manami Suzuki Remi Yamashita |
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Institution: | Department of Chemistry, Faculty of Science, Saitama University, Sakura-ku, Saitama, Saitama 338-8570, Japan |
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Abstract: | The reaction of trans-cyclooctene with S8O yielded a novel bicyclic 1,2,3-trithiolane and trans-9,10,11-trithiabicyclo6.3.0]undecane (7). Oxidation of the trithiolane with dimethyldioxirane yielded three monoxides, which are assigned to two isomeric 9-oxides, rel-(1R,8R,9S)-9-oxide (15) and rel-(1R,8R,9R)-9-oxide (16), and 10-oxide (17). Further oxidation of rel-(1R,8R,9S)-9-oxide (15) provided rel-(1R,8R,9S,11S)-9,11-dioxide (18) and rel-(1R,8R,9R,11S)-9,11-dioxide (19), while that of rel-(1R,8R,9R)-9-oxide (16) gave rel-(1R,8R,9R,11S)-9,11-dioxide (19) and rel-(1R,8R,9R,11R)-9,11-dioxide (20). The structures of 18 and 19 were determined by X-ray crystallography. The structures of other oxides were elucidated by the spectroscopic data and results of further chemical transformations. Two isomers, 15 and 16, isomerized to one another. A 9,11-dioxide 20 isomerized to 19, which is in equilibrium with 18, where 18 is thermodynamically the most stable isomer. |
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Keywords: | Trithiolane Cyclooctene Octasulfur monoxide Oxidation Isomerization |
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