SYNTHESIS OF 3-SILYLATED 3-SULFOLENES FROM PROPARGYLSILANES AND THEIR REDUCTIVE DESULFITATION

Authors

  • Rūdolfs Beļaunieks Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Mikus Puriņš Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Viktors Kumpiņš Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia
  • Māris Turks Associate Editor, Chemistry of Heterocyclic Compounds Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia

DOI:

https://doi.org/10.1007/5995

Keywords:

propargylsilanes, silyl sulfolenes, cheletropic addition, desulfitation, 1, 2-silyl migration.

Abstract

Protonation of propargylsilanes induces 1,2-silyl group shift and provides 2-silylated dienes. If this reaction is performed in liquid SO2, the diene formation is followed by instant cheletropic SO2 addition, and 3-silylated 3-sulfolenes are obtained. Liquid SO2 as polar and Lewis acidic reaction medium makes it possible to use relatively weak Brønsted acid catalysts such as H2O and benzoic acid. Depending on the starting material, reductive desulfitation of 3-silylated 3-sulfolenes provides vinyl, allyl, or aliphatic silanes.

Author Biography

Māris Turks, Associate Editor, Chemistry of Heterocyclic Compounds Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3 P. Valdena St., Riga LV-1048, Latvia

Full Professor

Institute of Technology of Organic Chemistry

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Published

2021-01-26

Issue

Vol. 57 No. 1 (2021)

Section

Original Papers