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

doi:10.1021/JO00220A006

Paper

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

Published 1985 · W. Adcock, V. S. Iyer, W. Kitching

Journal of Organic Chemistry

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Abstract

A specifically labeled H derivative of 1-bromo-4-iodobicyclo[2.2.2]octane has been synthesized and reacted with (trimethylstannyl)lithium. A full product and H-label profile has been established by H, H, C, and Sn 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 S1 mechanism for electron-transfer initiated aliphatic and aromatic nucleophilic substitutions.

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Trimethylstannylation of 1,4-dihalobicyclo[2.2.2]octanes involves a novel radical chain mechanism, involving radical anions and free radicals, rather than the intermediacy of [2.2.2]propellane.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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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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