Stereochemical aspects of sulfur dioxide insertion into cyclohex-2-enylstannanes

Young D. and Kitching W. (1988) Stereochemical aspects of sulfur dioxide insertion into cyclohex-2-enylstannanes. Organometallics, 7 5: 1196-1201.

Author Young D.
Kitching W.
Title Stereochemical aspects of sulfur dioxide insertion into cyclohex-2-enylstannanes
Journal name Organometallics   Check publisher's open access policy
ISSN 0276-7333
Publication date 1988-01-01
Sub-type Article (original research)
Volume 7
Issue 5
Start page 1196
End page 1201
Total pages 6
Subject 1604 Human Geography
1605 Policy and Administration
Abstract Sulfur dioxide insertion into a range of (4-alkylcyclohex-2-enyl)-, (5-alkylcyclohex-2-enyl)-, and (6-alkylcyclohex-2-enyl)stannanes has been studied for the solvents chloroform and methanol, and the reaction proceeds γ-regiospecifically (with allylic rearrangement) to provide the O-sulfinate. For chloroform solvent, syn stereospecificity was observed (and hence sulfur dioxide insertion is less sensitive to steric factors than trifluoroacetolysis) whereas for methanol solvent (despite γ-regiospecificity) insertion is not stereospecific, possibly reflecting the importance of methanol coordination at tin, reducing the necessity for intramolecular coordination and the consequential operation of the γ-syn stereocourse. Comparisons of the results for acidolysis and sulfur dioxide insertion of cyclohex-2-enylstannanes demonstrate that SE′ reactions lack a unique, stereoelectronically enforced stereochemical outcome and that factors such as the nature of the electrophile, solvent, steric factors, etc. may operate to render γ-syn and γ-anti stereocourses of comparable energies.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
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Citation counts: TR Web of Science Citation Count  Cited 9 times in Thomson Reuters Web of Science Article | Citations
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