Preparation, characterization and stereochemistry of 2-methyl-2-silabicyclo(2.2.1)heptane derivatives.

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概要

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• A new class of bicyclic compounds containing a single silicon atom at the bridge, 2-exo- and endo-substituted 2-methyl-2-silabicyclo[2.2.1]heptanes, have been prepared from the corresponding 3-cyclopentenyl-methylhydrosilane by the intramolecular hydrosilylation catalyzed by chloroplatinic acid, and their structures were unquivocally assigned by <SUP>1</SUP>H and <SUP>13</SUP>C NMR spectra. Dramatic crossover from inversion to retention was found in the phenylation of chlorosilanes with phenyllithium and phenylmagnesium bromide in ether. Regio- and stereoselective insertion of dichlorocarbene generated from phenyl(bromodichloromethyl)mercury, or from chloroform and sodium hydroxide in the presence of a phase transfer catalyst, into C<SUB>(6)</SUB>–H<SUB>(exo)</SUB> bond of 2-silanorbornanes has been observed.

• 公益社団法人 日本化学会の論文

著者

• Hosomi Akira

  Department Of Chemistry And Graduate School Of Chemistry University Of Tsukuba

• Sakurai Hideki

  Department Of Chemistiy Faculty Of Science Tohoku University

• Mikami Masashi

  Department of Chemistry, Faculty of Science, Tohoku University

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