Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution

Young D., Jones M. and Kitching W. (1985) Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution. Australian Journal of Chemistry, 39 4: 563-573. doi:10.1071/CH9860563


Author Young D.
Jones M.
Kitching W.
Title Carvone- and Piperitone-Derived Allylic Stannanes and Aspects of Their Electrophilic Substitution
Journal name Australian Journal of Chemistry   Check publisher's open access policy
ISSN 1445-0038
Publication date 1985
Sub-type Article (original research)
DOI 10.1071/CH9860563
Volume 39
Issue 4
Start page 563
End page 573
Total pages 11
Subject 1600 Chemistry
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.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
 
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