
%0 Journal Article
%A Young, D 
%A Jones, M 
%A Kitching, W 
%T Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
%J Australian Journal of Chemistry
%D 1986/04/01
%V 39
%N 4
%P 563-573
%K 
%R https://doi.org/10.1071/CH9860563
%U https://www.publish.csiro.au/paper/CH9860563 
%X cis - and trans- Carvotanacetols and - piperitols have been converted into the corresponding allylic chlorides, which were made to react with both trimethyltinlithium and triphenyltinlithium . The resulting allylic stannanes were characterized by 1H, 13C and 119Sn n.m.r . spectroscopy, which permitted assignment of the relative configurations. Triphenyltinlithium appears to react in a (substantially) concerted fashion with the (optically active) chloride from the carvotanacetols yielding an optically active stannane . The corresponding trimethylstannane is optically inactive. Substitution reactions (SE&#8242;) with acid and sulfur dioxide (in chloroform) are preferentially &#947;-anti and specifically &#947;- syn respectively, in line with conclusions based on other cyclohex-2-enyl systems. 
