[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts

Thies Thiemann, Jesus Iniesta, David J. Walton

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Cycloaddition reactions of 2,5-di-tert-butylthiophene S-oxide and 2,3,4,5-tetrakis(p-tolyl)thiophene S-oxide with alkenes are described. The reactivity of 2,5-di-tert-butylthiophene S-oxide as diene in Diels–Alder reactions is compared with 2,5-di-tert-butylthiophene S,S-dioxide. The thermal and photochemical SO extrusion reactions of the cycloadducts under formation of highly substitutedaromatic compounds are exemplified.

Original languageEnglish
Pages (from-to)876-884
Number of pages9
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume191
Issue number6
DOIs
Publication statusPublished - 2016
Externally publishedYes

Keywords

  • SO extrusion
  • Thiophene S,S-dioxide
  • cycloaddition
  • thiophene S-oxide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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