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Nucleophilic substitution reaction at an sp carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles |
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| Authors: | Mao-Yi Lei Wei-Min Liu Shunsuke Chiba Koichi Narasaka |
| Affiliation: | a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore b Department of Chemistry, Graduate School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan c Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido Gifu 501-1193, Japan |
| Abstract: | This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies. |
| Keywords: | Nucleophilic vinylic substitution Sulfur-containing heterocycles SNVσ and SNVπ mechanisms Density functional theory (DFT) |
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