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Note | Special issue | Vol 66, No. 1, 2005, pp.595-602
Published online, 1st November, 2005
DOI: 10.3987/COM-05-S(K)37
Reactions of 1,1-Bis(silylmethyl)-1-alkene with N-Halosuccinimide and Ozone

Jun’ichi Uenishi,* Yusuke Tanaka, Masashi Ohmi, Hotsumi Shimomura, and Nobuyuki Kawai

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-1-pentene (5) and 3-halo-5-phenyl-1,2-bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).