(Alk-1-ynyl)organylthiocarbenes: generation and reactions with olefins |
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Authors: | K N Shavrin V D Gvozdev I Yu Pinus I P Dotsenko O M Nefedov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820 Moscow, Russian Federation |
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Abstract: | 1-Substituted 1-chloro-3-organylthiopropa-1,2-dienes 1a–f belonging to previously unknown type of allenic compounds were synthesized by chlorination of 1-organylthioalk-1-ynes 3a–f with N-chlorosuccinimide. The reactions of compounds 1a–f with ButOK in hexane at –20 °C are accompanied by -elimination of HCl to give new alk-1-ynyl(organylthio)carbenes 2a–f, which add to olefins to form the corresponding 1-(alk-1-ynyl)-1-organylthiocyclopropanes 5 in yields of up to 60%. The electrophilic properties of carbenes 2 were confirmed experimentally.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2440–2447, November, 2004. |
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Keywords: | 1-substituted 1-chloro-3-organylthiopropa-1 2-dienes alkyn-1-yl(organylthio)carbenes 1-(alkyn-1-yl)-1-organylthiocyclopropanes [1+2] cycloaddition electrophilic carbenes |
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