THE EFFECT OF POLAR SUBSTITUENTS ON THE CONFORMATION AND STEREOCHEMISTRY OF ENOLATE RADICALS

Authors
GIESE B DAMM W WETTERICH F ZEITZ HG RANCOURT J GULNDON Y
Citation
B. Giese et al., THE EFFECT OF POLAR SUBSTITUENTS ON THE CONFORMATION AND STEREOCHEMISTRY OF ENOLATE RADICALS, Tetrahedron letters, 34(37), 1993, pp. 5885-5888
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
37
Year of publication
1993
Pages
5885 - 5888
Database
ISI
SICI code
0040-4039(1993)34:37<5885:TEOPSO>2.0.ZU;2-V
Abstract
ESR measurements and AM1 calculations show that ester substituted radi cals 2 and 6 prefer conformation A as a result of allylic strain effec ts. But dipolar repulsion between substituents X and CO2Et in 2 and 6 has a pronounced effect on the conformation and the stereoselectivity of radicals 2 and 6.