Oxidative cycloaddition of molecules with multiple thiophene cores

Thies Thiemann, Yuanqiang Li, Carolin Thiemann, Tsuyoshi Sawada, Daisuke Ohira, Masashi Tashiro, Shuntaro Mataka

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


The oxidative cycloaddition of molecules with multiple thienyl-units to alkynes and alkenes is described. The reaction proceeds at room temperature. Yields can be increased upon the use of BF3·Et2O. Intermediates of the reaction are thiophene-S-oxides. An examplary isolation of a thiophene-S- oxide (16) in this series and its subsequent cycloaddition are shown. In the case of the oxidative cycloaddition of the thiophenes with alkenes 7- thiabicyclo[2.2.1]heptene-S-oxides (cf., 9) are formed. An X-Ray crystal structural analysis of 9a-H indicates the cycloaddition to be stereoselective (syn-endo). The SO-bridge in these bicyclic subunits could be extruded both thermally and oxidatively under PTC-conditions at room temperature. The products are novel orthocyclophanes.

Original languageEnglish
Pages (from-to)1215-1230
Number of pages16
Issue number3
Publication statusPublished - Mar 1 2000
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry


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