OPENING OF THE FURAN RING OF 3-NITROBENZOFURANS BY THE ACTION OF CARBONYL-STABILIZED SULFONIUM YLIDES

Authors

  • Ирина А. Семенова Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Виталий А. Осянин Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia
  • Олег П. Демидов North Caucasus Federal University, 1a Pushkina St., Stavropol 355009, Russia
  • Дмитрий В. Осипов Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

DOI:

https://doi.org/10.1007/6613

Keywords:

dimethylphenacylsulfonium salts, 3-nitrobenzofurans, sulfur ylides, Michael reaction, nucleophilic dearomatization.

Abstract

Upon treatment of 3-nitrobenzofurans with dimethylphenacylsulfonium salts in the presence of a base, the opening of the furan ring to form (E)-1-aryl-2-(dimethylsulfonio)-4-nitro-1-oxobut-3-en-2-ides takes place. The mechanism of nucleophilic dearomatization of 3-nitrobenzofurans involves consecutive carbo- and retro-oxa-Michael reactions. The reaction illustrates the high propensity of 3-nitrobenzofurans for ring opening.

Author Biographies

Ирина А. Семенова, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

аспирант

Виталий А. Осянин, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

д.х.н., профессор

Олег П. Демидов, North Caucasus Federal University, 1a Pushkina St., Stavropol 355009, Russia

д.х.н., профессор

Дмитрий В. Осипов, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia

к.х.н., доцент

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Published

2022-05-18

Issue

Vol. 58 No. 4/5 (2022)

Section

Short Communications