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Paper | Special issue | Vol 88, No. 1, 2014, pp.453-462
Published online, 29th July, 2013
DOI: 10.3987/COM-13-S(S)53
Study on Hinsberg Thiophene Synthesis of 4,8-Dihydro-4,8-ethanobenzo[1,2-c;4,5-c’]dithiophene

Kazunari Tagawa, Shigeki Mori, Takahiro Nakae, Tetsuo Okujima, and Hidemitsu Uno*

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan

Abstract

The Hinsberg thiophene synthesis using 4,5,6,7-tetrahydro-4,7-ethanothiophene-5,6-dione and diethyl thiodiglycolate afforded a mixture of diethyl 4,8-dihydro-4,8-ethanobenzo[1,2-c;4,5-c’]dithiophene-1,3-dicarboxylate and its dihydrate, although the yields were low. The latter dihydrate was converted to the former dithiophene in a good yield by the treatment with Ac2O and DMAP.