Journal article
Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
Australian Journal of Chemistry, Vol.39(4), pp.563-573
1986
Abstract
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′) with acid and sulfur dioxide (in chloroform) are preferentially γ-anti and specifically γ- syn respectively, in line with conclusions based on other cyclohex-2-enyl systems.
Details
- Title
- Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
- Authors
- David James Young (Author) - University of QueenslandM Jones (Author) - University of QueenslandW Kitching (Author) - University of Queensland
- Publication details
- Australian Journal of Chemistry, Vol.39(4), pp.563-573
- Publisher
- C S I R O Publishing
- Date published
- 1986
- DOI
- 10.1071/CH9860563
- ISSN
- 0004-9425
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449401402621
- Output Type
- Journal article
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