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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Stannylation and germylation of some 4-, 5- and 6-Alkylcyclohex-2-enyl chlorides

D Young, W Kitching and G Wickham

Australian Journal of Chemistry 37(9) 1841 - 1862
Published: 1984

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.

https://doi.org/10.1071/CH9841841

© CSIRO 1984

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