Russian Journal of Organic Chemistry

, Volume 38, Issue 7, pp 970–976

Reactions of 2-Alkoxypropenals with Thiols in Neutral and Acid Media

  • N. A. Keiko
  • E. A. Funtikova
  • L. G. Stepanova
  • Yu. A. Chuvashev
  • L. I. Larina
Article

DOI: 10.1023/A:1020893310626

Cite this article as:
Keiko, N.A., Funtikova, E.A., Stepanova, L.G. et al. Russian Journal of Organic Chemistry (2002) 38: 970. doi:10.1023/A:1020893310626

Abstract

Addition of thiols to 2-alkoxypropenal in neutral medium at 20°C in the absence of a catalyst occurs regioselectively, following the Markownikoff pattern. The resulting 2-alkoxy-2-R-thiopropanals are capable of undergoing spontaneous isomerization to 1-alkoxy-1-R-thiopropanones. The addition and isomerization processes are accelerated by heating to 60°C or in the presence of acid catalysts (TsOH, HCl). The reaction is also accompanied by partial disproportionation of 2-oxopropanal O,S-acetals to give O,O- and S,S-acetals.

Copyright information

© MAIK “Nauka/Interperiodica” 2002

Authors and Affiliations

  • N. A. Keiko
    • 1
  • E. A. Funtikova
    • 1
  • L. G. Stepanova
    • 1
  • Yu. A. Chuvashev
    • 1
  • L. I. Larina
    • 1
  1. 1.Irkutsk Institute of Chemistry, Siberian DivisionRussian Academy of SciencesIrkutsk