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Configurational stability of the unsubstituted cyclopropyl radical in the Hunsdiecker reaction

โœ Scribed by Kobayashi, Keiji; Lambert, Joseph B.


Book ID
115491135
Publisher
American Chemical Society
Year
1977
Tongue
English
Weight
393 KB
Volume
42
Category
Article
ISSN
0022-3263

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Configurational stability of cyclopropyl
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Cyclopropyl radicals normally undergo complete thermodynamic equilibration of configuration before they react, e.g., with bromine in the Hunsdiecker reaction'. Incomplete equilibration is normally due to steric or cage effectsa, and to surface effects when cyclopropyl halides are reduced with metals

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The effect of an electron withdrawing group adjacent to cyclopropyl carbanion has been studied. The facilitv with which carbanion interconversion occurs can be attributed to the existence of"the anomeric effect. Cyclopropyl carbanions derived from optically active precursors are capable of retaining