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

T. Thiemann, J. Iniesta, David Walton

Research output: Contribution to journalArticle

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

Fingerprint

Thiophenes
Cycloaddition
Cycloaddition Reaction
Alkenes
Oxides
Extrusion
Hot Temperature

Keywords

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

Cite this

[4+2]-Cycloaddition of sterically hindered thiophene S-oxides to alkenes and SO extrusion reactions of the cycloadducts. / Thiemann, T.; Iniesta, J.; Walton, David.

In: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol. 191, No. 6, 2016, p. 876-884.

Research output: Contribution to journalArticle

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AU - Iniesta, J.

AU - Walton, David

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AB - 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.

KW - Thiophene S

KW - S-dioxide

KW - thiophene S-oxide

KW - cycloaddition

KW - SO extrusion

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