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

T. Thiemann, J. Iniesta, David Walton

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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
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume191
Issue number6
DOIs
Publication statusPublished - 2016

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Keywords

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

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