Journal article
Mechanistic definition of trimethylstannylation of 1,4-dihalobicyclo[2.2.2]octanes: A labeling experiment excludes intermediacy of [2.2.2]propellane but suggests a novel radical chain mechanism
Journal of Organic Chemistry, Vol.50(20), pp.3706-3710
1985
Abstract
A specifically labeled 2H derivative of 1-bromo-4-iodobicyclo[2.2.2]octane has been synthesized and reacted with (trimethylstannyl)lithium. A full product and 2H-label profile has been established by 1H, 2H, 13C, and 119Sn NMR spectroscopy, and the intermediacy of [2.2.2]propellane can be disregarded. The results, along with others for additional 1,4-dihalobicyclo[2.2.2]octanes, are best accommodated by a chain mechanism (involving radical anions and free radicals) somewhat akin to the S RN1 mechanism for electron-transfer initiated aliphatic and aromatic nucleophilic substitutions. © 1985 American Chemical Society.
Details
- Title
- Mechanistic definition of trimethylstannylation of 1,4-dihalobicyclo[2.2.2]octanes: A labeling experiment excludes intermediacy of [2.2.2]propellane but suggests a novel radical chain mechanism
- Authors
- W Adcock (Author) - University of South AustraliaV S Iyer (Author) - University of South AustraliaW Kitching (Author) - University of QueenslandDavid James Young (Author) - University of Queensland
- Publication details
- Journal of Organic Chemistry, Vol.50(20), pp.3706-3710
- Publisher
- American Chemical Society
- Date published
- 1985
- DOI
- 10.1021/jo00220a006
- ISSN
- 0022-3263
- Organisation Unit
- University of the Sunshine Coast, Queensland
- Language
- English
- Record Identifier
- 99449123302621
- Output Type
- Journal article
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- Chemistry, Organic
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Source: InCites