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

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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

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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
Author/Creator: Adcock, W | Iyer, V S | Kitching, W | Young, David James
Description: 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.
Relation: Journal of Organic Chemistry / Vol. 50, No. 20, pp.3706-3710
Relation: http://dx.doi.org/10.1021/jo00220a006
Year: 1985
Publisher: American Chemical Society
Subject: FoR 0304 (Medicinal and Biomolecular Chemistry) | FoR 0305 (Organic Chemistry) | nucleophilic substitutions

Resource Type: Journal Article
Identifier: ISSN: 0022-3263
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