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

David James Young; W Kitching; G Wickham

doi:10.1071/CH9841841

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

Journal article

Peer reviewed

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

David James Young, W Kitching and G Wickham

Australian Journal of Chemistry, Vol.37(9), pp.1841-1862

1984

DOI: https://doi.org/10.1071/CH9841841

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Abstract

Chemical Sciences

allylic alcohols

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.

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Title: Stannylation and germylation of some 4-, 5- and 6-Alkylcyclohex-2-enyl chlorides
Authors: David James Young (Author) - University of Queensland
W Kitching (Author) - University of Queensland
G Wickham (Author) - University of Queensland
Publication details: Australian Journal of Chemistry, Vol.37(9), pp.1841-1862
Publisher: C S I R O Publishing
Date published: 1984
DOI: 10.1071/CH9841841
ISSN: 0004-9425
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450089602621
Output Type: Journal article

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