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ONLINEISSN:1348-0715
PRINTISSN:0366-7022
Chemistry Letters
Vol. 36 (2007) , No. 7 p.820
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Participation of Geminal Bonds in Organic Reactions
Yuji Naruse1) and Satoshi Inagaki1)
1) Department of Chemistry, Gifu Univerisity
(Received May 2, 2007)

The σ-bonds geminal to the π-reacting center have been proposed to participate in the organic reactions via the cyclic transition states and to control the reactivity and the selectivity. An electron-donating geminal σ bond at the Z position enhances the reactivity of the olefins. An electron-donating σ bond prefers the Z position of the π bond in the products of the reverse reactions. The effects of the geminal bond participation come from the orbital phase properties of the cyclic interactions including the geminal σ bonds.

 

 


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doi:10.1246/cl.2007.820
JOI  JST.JSTAGE/cl/2007.820
Copyright (c) 2007 The Chemical Society of Japan



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