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Paper | Special issue | Vol 74, No. 1, 2007, pp.863-872
Published online, 30th November, 2007
DOI: 10.3987/COM-07-S(W)82
Synthesis of 1,1-Dichloro-2,5-diphenylsilacyclopent-3-enes by the Chlorination of 1,1-Diethoxy- and Bis(optically Active Alkoxy)-2,5-diphenylsilacyclopent-3-enes

Kenichi Miyakawa, Chihiro Fujii, Koji Arimitsu, and Yukinori Nagao*

*Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


The 1,1-diethoxy-2,5-diphenylsilacyclopent-3-ene was reacted with optically active alcohols ((-)-menthol, (-)-borneol, (-)-amyl alcohol ) to obtain the corresponding 1,1-bis(optically active alkoxy)-2,5-diphenyl-silacyclopent-3-enes including various ratios of diastereomers. The 1,1-diethoxy and dialkoxy-2,5-diphenylsilacyclopent-3-enes were reacted with acetylchloride in the presence of zinc chloride to produce 1,1-dichloro-2,5-diphenyl-silacyclopent-3-ene having reactive substituents including various ratios of diastreomers.