Journal article
Synthesis and electrophilic cleavage of some verbenylstannanes
Journal of Organic Chemistry, Vol.50(21), pp.4098-4102
1985
Abstract
Trifluoroacetolysis of the allylic cis- and trans-verbenylstannanes yields a mixture of cis- and trans-δ-pinenes, confirming regiospecific γ-substitution. Analysis of the product distribution confirms the view that any inherent preference for γ-anti substitution (anti-SE′ process) is not so strong that steric effects on both reagent approach and product development cannot influence the balance between syn and anti stereocourses. Sulfur dioxide insertion (chloroform solvent) proceeds readily with the trans-stannane to provide the rearranged (tertiary) "δ-pinenylsulfinate" in a stereospecific syn fashion (syn-SE′ process). cis-Verbenylstannane is less reactive but is transformed to the same sulfinate. The verbenylstannanes were acquired by trimethyl- and triphenylstannylation (with (trimethyltin)lithium and (triphenyltin)lithium in tetrahydrofuran) of predominantly (∼90%) trans-verbenyl chloride. © 1985 American Chemical Society.
Details
- Title
- Synthesis and electrophilic cleavage of some verbenylstannanes
- Authors
- David James Young (Author) - University of QueenslandW Kitching (Author) - University of Queensland
- Publication details
- Journal of Organic Chemistry, Vol.50(21), pp.4098-4102
- Publisher
- American Chemical Society
- Date published
- 1985
- DOI
- 10.1021/jo00221a026
- ISSN
- 0022-3263
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449204602621
- Output Type
- Journal article
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- Chemistry, Organic
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