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Paper | Regular issue | Vol 85, No. 5, 2012, pp.1077-1088
Published online, 22nd March, 2012
DOI: 10.3987/COM-12-12427
Synthesis of Fluorene- and Spirobifluorene-Fused Thiophenes

Wen Yao, Qiancai Liu,* Yingbo Shi, and Jie Tang

*Department of Chemistry, East China Normal University, 500 Dongchuan Rd., Minhang, Shanghai 200241, China

Abstract

A novel synthetic route to fluorene- and spirobifluorene-fused thiophenes is explored by starting with ninhydrin. The Diels-Alder cycloaddition was employed to construct the key intermediate, 2,3-bis(hydroxymethyl)-1,4-diphenyl-fluorenone, which was further converted stepwise to the target molecules. All of dihydrothiophenes and final products are confirmed by 1H NMR, 13C NMR and mass spectrometry.