Stereochemical studies with 1,2,5-trimethyl-1-silacyclopentanes

Franke F. and Wells P.R. (1979) Stereochemical studies with 1,2,5-trimethyl-1-silacyclopentanes. Journal of Organic Chemistry, 44 23: 4055-4060.

Author Franke F.
Wells P.R.
Title Stereochemical studies with 1,2,5-trimethyl-1-silacyclopentanes
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 1979-01-01
Sub-type Article (original research)
Volume 44
Issue 23
Start page 4055
End page 4060
Total pages 6
Subject 1605 Policy and Administration
Abstract Chlorination of 1,2,5-trimethyl-1-silacyclopentane by benzoyl peroxide/carbon tetrachloride proceeds with 100% retention of configuration at silicon, but reaction with triphenylmethyl chloride in benzene gives two-thirds retention and one-third inversion. 1-Chloro-1,2,5-trimethyl-1-silacyclopentane isomerizes slowly in nonpolar solvents, but salts strongly enhance the rate of isomerization. Displacement of chloride by fluoride and by methoxide is nonstereospecific but, in the case of the latter, is stereoselective. Displacement of chloride by acetate proceeds with predominant inversion of configuration at silicon. The kinetics of the isomerization of 1-acetoxy-1,2,5-trimethyl-1-silacyclopentane by methoxide have been studied.
Q-Index Code C1
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import - Archived
 
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Created: Tue, 13 Sep 2016, 12:15:20 EST by System User