ADDITION OF 1,2- AND 1,3-DITHIOLS TO 2-ALKOXYPROPENALS – A NEW METHOD FOR THE PRODUCTION OF SUBSTITUTED DITHIACYCLOALKANES

Authors

  • Н. А. Кейко A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk
  • Е. А. Фунтикова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk
  • Л. Г. Степанова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk
  • Ю. А. Чувашев A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk
  • Л. И. Ларина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk

Keywords:

2-alkoxypropenals, 1,3- and 1,4-dithiane, 1,3-dithiolane, 1,2- and 1,3-dithiols

Abstract

The reaction of 2-alkoxypropenals with ethane-1,2-dithiols and propane-1,3-dithiols under various conditions was studied by 1H NMR and chromato-mass spectrometry. Under kinetically controlled conditions at 20°C in the absence of catalysts the addition of dithiols takes place according to the Markovnikov rule. The primary adducts are unstable and are quickly converted into the corresponding substituted 1,4-dithiacycloheptane or 1,4-dithiane. The latter in turn can be converted under the reaction conditions or at high temperature into a thiolane derivative. The reaction of 2-ethoxypropenal with a twofold excess of ethane-1,2-dithiol at 60°C in the presence of p-toluenesulfonic acid leads to 2-methyl-2,2'-bi(dithiolane).

How to Cite
Keiko, N. A.; Funtikova, E. A.; Stepanova, L. G.; Chuvashev, Yu. A.; Larina, L. I. Chem. Heterocycl. Compd. 2002, 38, 390. [Khim. Geterotsikl. Soedin. 2002, 455.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1016066918919

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Published

2002-04-25

Issue

No. 4 (2002)

Section

Original Papers