FIRST EXAMPLE OF THE SYNTHESIS OF N-VINYLPYRROLE FROM METHOXYALLENE AND METHOXYETHYL ISOTHIOCYANATE: UNPRECEDENTED ELIMINATION OF METHANOL FROM A β-SUBSTITUTED METHYL ETHYL ETHER

Authors

  • Н. А. Недоля Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • О. А. Тарасова Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • А. И. Албанов Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • Л. В. Клыба Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
  • Б. А. Трофимов Irkutsk A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences

DOI:

https://doi.org/10.1007/2781

Keywords:

N-vinylpyrrole, methoxyallene, N-(2-methoxyethyl)pyrrole, 2-methoxyethyl isothiocyanate, t-BuOK–DMSO system, synthesis, β-elimination

Abstract

Using as example 3-methoxy-1-(2-methoxyethyl)-2-methylsulfanylpyrrole, obtained in one preparative stage from α-lithiated methoxyallene and 2-methoxyethyl isothiocyanate, a facile cleavage of a C–O bond in the N-(2-methoxyethyl) substituent by the t-BuOK–DMSO system has been discovered, opening access to a new class of N-vinylpyrroles (through β-elimination of methanol).

How to Cite
Nedolya, N. A.; Tarasova, O. A.; Albanov, A. I.; Klyba, L. V.; Trofimov, B. A. Chem. Heterocycl. Compd. 2010, 46, 61. [Khim. Geterotsikl. Soedin. 2010, 72.]

For this article in the English edition see DOI 10.1007/s10593-010-0470-9

Downloads

Published

2015-11-25

Issue

No. 1 (2010)

Section

Original Papers