Thorpe-Ingold effect in the reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide |
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Authors: | Ning ChenZhongyan Huang Chan ZhouJiaxi Xu |
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Institution: | State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, PR China |
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Abstract: | The Thorpe-Ingold effect is a key factor that affects the ring-closure rates and efficiency, as well as the structure of products in some ring-closure reactions. The reaction of vicinal amino primary alcohol hydrogen sulfates and carbon disulfide in the presence of potassium hydroxide produces the desired 4,4-disubstituted thiazolidine-2-thiones, and their isomers 5,5-disubstituted derivatives companying with their oxygen analogues 4,4-disubstituted oxazolidine-2-thiones. The formation of 5,5-disubstituted thiazolidine-2-thiones was rationalized via 2,2-disubstituted aziridine-1-carbodithioate intermediates, which were generated due to the Thorpe-Ingold effect. 4,4-Disubstituted oxazolidine-2-thiones were generated from carbon disulfide and free amino alcohols yielded via basic hydrolysis of active amino alcohol hydrogen sulfates in the reaction system. |
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Keywords: | Amino alcohol hydrogen sulfate Aziridine Oxazolidine-2-thione Thiazolidine-2-thione Thorpe-Ingold effect |
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