Novel Synthesis and Bridgehead Functionalization of Permethylbicyclo[2.2.2]octasilane

Selective bridgehead chlorination of permethylbicyclo[2.2.2]octasilane 1 giving the corresponding 1-chloro- (2a) and 1,4-dichlorobicyclooctanes 3a was achieved using BCl3 in chloroform. 1-Chlorobicyclooctane 2a resists the reactions with various nucleophiles such as phenyllithium and lithium aluminu...

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Bibliographic Details
Published in:Chemistry letters 2004-05, Vol.33 (5), p.626-627
Main Authors: Setaka, Wataru, Hamada, Natsuki, Kira, Mitsuo
Format: Article
Language:English
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Summary:Selective bridgehead chlorination of permethylbicyclo[2.2.2]octasilane 1 giving the corresponding 1-chloro- (2a) and 1,4-dichlorobicyclooctanes 3a was achieved using BCl3 in chloroform. 1-Chlorobicyclooctane 2a resists the reactions with various nucleophiles such as phenyllithium and lithium aluminum hydride but reacts with KC8 affording the corresponding silylpotassium 2b in quantitative yield.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2004.626