Stannylation and Germylation of Some 4-, 5- and 6-Alkylcyclohex-2-enyl Chlorides

Young D., Kitching W. and Wickham G. (1984) Stannylation and Germylation of Some 4-, 5- and 6-Alkylcyclohex-2-enyl Chlorides. Australian Journal of Chemistry, 37 9: 1841-1862. doi:10.1071/CH9841841


Author Young D.
Kitching W.
Wickham G.
Title Stannylation and Germylation of Some 4-, 5- and 6-Alkylcyclohex-2-enyl Chlorides
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 1445-0038
Publication date 1984
Sub-type Article (original research)
DOI 10.1071/CH9841841
Volume 37
Issue 9
Start page 1841
End page 1862
Total pages 22
Subject 1600 Chemistry
Abstract The allylic alcohols, trans-5-t-butylcyclohex-2-enol, trans-4-t-butylcyclohex-2-enol and trans-4- methylcyclohex-2-enol, have been converted into cyclohex-2-enyl chlorides by reaction with thionyl chloride and N-chlorosuccinimide-dimethyl sulfide. The stereochemistry of the allylic chlorides has been determined by 1H and 13C nuclear magnetic resonance spectroscopy. Stannylation of these chlorides with trimethyltinlithium, and triphenyltinlithium, has been examined and the resulting stannanes fully characterized by 1H, 13C and 119Sn n.m.r. spectroscopy, and electrophilic cleavage (acidolysis with deuterated trifluoroacetic acid) to the corresponding deuterocyclohexenes. A less extensive study of germylation (trimethylgermyllithium in hexamethylphosphoramide) was conducted also, and the allylic germanes fully characterized. Triphenyltinlithium and trimethylgermyllithium exhibit higher levels of stereo- and regio-specificity in chloride displacement than trimethyltinlithium.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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Created: Tue, 14 Jun 2016, 05:16:35 EST by System User