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Communication | Special issue | Vol 82, No. 2, 2011, pp. 1103 - 1112
Published online: 20th August, 2010
DOI: 10.3987/COM-10-S(E)70
■ Unexpected Formation of Dihydrobenzosilole Derivative via the Intramolecular Cyclization in the Reaction of Overcrowded Dichloromethylsilane with Aryllithium

Takahiro Sasamori,* Eiko Mieda, and Norihiro Tokitoh*

*Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan

Abstract

The reaction of overcrowded aryldichloromethylsilane 1 bearing a 2,6-bis[bis(trimethylsilyl)methyl]-4-[tris(trimethylsilyl)methyl]phenyl (Bbt) group with an excess amount of XylLi or MesLi (Xyl = 2,6-xylyl, Mes = mesityl) unexpectedly afforded the corresponding dihydrobenzosilole derivative 2 together with silyl-migrated olefin 3. The generation of 2 in this reaction is most likely interpreted in terms of intermediacy of 1,2-dihydro-2-chlorosilene 4.

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