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Orbital‐Overlap Control of the Reactivity of a Bicyclic 1‐Hydroxy‐1,4‐Biradical
Author(s) -
Yang Chao,
Xia Wujiong,
Scheffer John R.,
Botoshansky Mark,
Kaftory Menahem
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200500983
Subject(s) - cleavage (geology) , bicyclic molecule , enantiomer , reactivity (psychology) , stereochemistry , chemistry , materials science , medicine , alternative medicine , pathology , fracture (geology) , composite material
Radical reform : Cleavage of the enantiotopic C2C3 or C2C3′ bonds in bicyclic 1‐hydroxy‐1,4‐biradicals (see structure) leads to enantiomeric products. Absolute configuration correlations demonstrate that, in the crystalline state, cleavage occurs mainly in one direction and is controlled by the orientation of the cleaving bonds with respect to the p orbital at the C1 position.