C-C BOND-CLEAVAGE IN O-CENTERED MONO- AND DIANIONS DERIVED FROM ALPHA-DICARBONYL COMPOUNDS

Authors
VAREA T MEDIO M BALLESTEROS R ONIGA O ASENSIO G
Citation
T. Varea et al., C-C BOND-CLEAVAGE IN O-CENTERED MONO- AND DIANIONS DERIVED FROM ALPHA-DICARBONYL COMPOUNDS, Tetrahedron, 51(36), 1995, pp. 10093-10100
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
36
Year of publication
1995
Pages
10093 - 10100
Database
ISI
SICI code
0040-4020(1995)51:36<10093:CBIOMA>2.0.ZU;2-L
Abstract
The reaction of organolithium compounds with oxalyl derivatives and cy clic 1,2-dicarbonyl compounds leads to pinacols or ketones derived fro m homolytic C-C bond cleavage of the intermediate O,O-centered pinacol dianions depending on the ability of the substituents for the stabili sation of the resulting radical anion. The homolysis is induced by ele ctrostatic repulsion of the negatively charged oxygen atoms.