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Paper | Special issue | Vol 52, No. 3, 2000, pp.1215-1230
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S134
Oxidative Cycloaddition of Molecules with Multiple Thiophene Cores

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

*Instituete of Advanced Material Study, Kyushu University, 6-1, Kasuga-koen, Kasuga-shi, Fukuoka 816-0811, Japan


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 FTC-conditions at room temperature. The products are novel orthocyclophanes.