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Synthesis 2011(3): 397-408  
DOI: 10.1055/s-0030-1258391
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Multi-Substituted Cyclobutanes and Alkylidenecyclobutanes by the Reaction of Cyclobutylmagnesium Carbenoids with Nucleophiles

Tsuyoshi Satoh*, Takashi Kasuya, Masashi Ishigaki, Mio Inumaru, Toshifumi Miyagawa, Nobuhito Nakaya, Shimpei Sugiyama
Graduate School of Chemical Sciences and Technology, Tokyo University of Science, Ichigaya-Funagawara-machi 12, Shinjuku-ku, Tokyo 162-0826, Japan
Fax: +81(3)52614631; e-Mail: tsatoh@rs.kagu.tus.ac.jp;
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Publication History

Received 18 October 2010
Publication Date:
10 January 2011 (online)

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Abstract

Treatment of 1-chlorocyclobutyl p-tolyl sulfoxides with Grignard reagents such as ethylmagnesium chloride, isopropylmagnesium chloride, and cyclopentylmagnesium chloride in THF at low temperature gave cyclobutylmagnesium carbenoids in high yields. The generated magnesium carbenoids were found to be stable at -78 ˚C for at least 30 minutes. The cyclobutylmagnesium carbenoids reacted with several nucleophiles to give multi-substituted cyclobutanes. The reaction of the cyclobutylmagnesium carbenoids with lithium α-sulfonyl carbanions afforded alkylidenecyclobutanes in moderate to good yields.

Key words

cyclobutane - alkylidenecyclobutane - magnesium carbenoid - cyclobutylmagnesium carbenoid - cyclobutylmagnesium chloride

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