Discovery and synthetic applications of novel silicon-carbon bond cleavage reactions based on the coordination number change of organosilicon compounds

Some synthetically useful transformations of organosilicon compounds have been developed since the mid 1970s, based on the new concept that the silicon-carbon bonds are activated toward electrophilic cleavage via the formation of penta- and hexa-coordinate species. This review mainly consists of the...

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Bibliographic Details
Published in:Proceedings of the Japan Academy, Series B Series B, 2008/05/30, Vol.84(5), pp.123-133
Main Author: TAMAO, Kohei
Format: Article
Language:English
Subjects:
Carbon - chemistry
Hydrogen Peroxide - chemistry
hydrogen peroxide oxidation
hypercoordination
intramolecular hydrosilylation
organopentafluorosilicate
organosilicon chemistry
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Oxidation-Reduction
Review
Silicon - chemistry
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Summary:Some synthetically useful transformations of organosilicon compounds have been developed since the mid 1970s, based on the new concept that the silicon-carbon bonds are activated toward electrophilic cleavage via the formation of penta- and hexa-coordinate species. This review mainly consists of the following aspects: (1) a general concept for the activation of the silicon-carbon bond via penta- and hexa-coordinate species, (2) synthetic application of hexa-coordinate organopentafluorosilicates, and (3) development of the H2O2 oxidation of the silicon-carbon bond and its synthetic applications via the intramolecular hydrosilylation, silicon-tethered intramolecular radical cyclization and Diels-Alder reaction, and some silicon-containing organometallic reagents for nucleophilic hydroxymethylation and hydroxyallylation synthons. (Communicated by Hitosi NOZAKI, M.J.A.)
ISSN:0386-2208
1349-2896
DOI:10.2183/pjab.84.123