Cycloaddition of thiophene S-oxides to allenes, alkynes and to benzyne

Thies Thiemann, Hideki Fujii, Daisuke Ohira, Kazuya Arima, Yuanqiang Li, Shuntaro Mataka

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

Thiophenes have been treated with alkynes in the presence of m-chloroperoxybenzoic acid to give substituted arenes as cycloadducts. Alternatively, thiophene S-oxides have been prepared by oxidation from thiophenes and have been subjected to cycloaddition with alkynes in a subsequent step. The outcome of the reaction is dependent on the steric demand of the thiophene S-oxide. Some thiophene S-oxides can be reacted at temperatures as high as 140°C without decomposition. Thiophenes as deoxygenated products are the main by-products. Reactions of thiophene S-oxides with allenes give in part thiabicyclo[2.2.1]heptene S-oxides of type 12a and 13 along with aromatized products. Thiophene S-oxides also cycloadd to benzyne.

Original languageEnglish
Pages (from-to)1377-1384
Number of pages8
JournalNew Journal of Chemistry
Volume27
Issue number9
DOIs
Publication statusPublished - Sep 2003
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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