Synthesis and electrophilic cleavage of some verbenylstannanes

Young D. and Kitching W. (1985) Synthesis and electrophilic cleavage of some verbenylstannanes. Journal of Organic Chemistry, 50 21: 4098-4102.

Author Young D.
Kitching W.
Title Synthesis and electrophilic cleavage of some verbenylstannanes
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 1985-01-01
Sub-type Article (original research)
Volume 50
Issue 21
Start page 4098
End page 4102
Total pages 5
Subject 1605 Policy and Administration
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.
Q-Index Code C1
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collection: Scopus Import
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Citation counts: TR Web of Science Citation Count  Cited 8 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 7 times in Scopus Article | Citations
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