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Nucleophilic substitution at an sp carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes |
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| Authors: | Mao-Yi Lei Yong-Jun Xiao Scott Twiddy Kaori Ando |
| Institution: | 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: | Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies. |
| Keywords: | Nucleophilic vinylic substitution 2-Alkylidenethietane SNVπ mechanism Density functional theory (DFT) |
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