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Short Paper | Regular issue | Vol 87, No. 11, 2013, pp.2333-2341
Published online, 16th October, 2013
DOI: 10.3987/COM-13-12813
■ Synthesis of 1,4-Diarylfluorenone and 1,4-Diarylfluorene

Yanmei Wang, Qiancai Liu,* Xiaoli Xiong, Shiming Deng, Jun Zhang, Min Zhu, and Hangmin Ge

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

Abstract

A novel synthetic route to 1,4-diarylfluorenone and 1,4-diarylfluorene is presented by starting with ninhydrin. The retro-Diels-Alder cycloaddition was employed as a key step to construct the target fluorenones, while a highly efficient reduction from 1,4-diarylfluorenones to 1,4-diarylfluorenes is developed by using of sodium sulfide nonahydrate as reductant. The final products are confirmed by 1H NMR, 13C NMR and mass spectrometry.