
TY  - JOUR
A1  - Young, D 
A1  - Jones, M 
A1  - Kitching, W 
T1  - Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1986
VL  - 39
IS  - 4
SP  - 563
EP  - 573
KW  - 
UR  - https://doi.org/10.1071/CH9860563 
N2  - 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. 
ER  -

