ORIGIN OF THE STEREOSELECTIVITY IN (ETHOXYCARBONYL)-SUBSTITUTED, CYANO-SUBSTITUTED, AND PHENYL-SUBSTITUTED (ARYLSULFINYL)METHYL RADICALS

Authors
RENAUD P BOURQUARD T CARRUPT PA GERSTER M
Citation
P. Renaud et al., ORIGIN OF THE STEREOSELECTIVITY IN (ETHOXYCARBONYL)-SUBSTITUTED, CYANO-SUBSTITUTED, AND PHENYL-SUBSTITUTED (ARYLSULFINYL)METHYL RADICALS, Helvetica Chimica Acta, 81(6), 1998, pp. 1048-1063
Citations number
40
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
81
Issue
6
Year of publication
1998
Pages
1048 - 1063
Database
ISI
SICI code
0018-019X(1998)81:6<1048:OOTSI(>2.0.ZU;2-P
Abstract
An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfinyl)methyl radicals is pr esented, based on experimental results and semiempirical calculations. The influence of dipole-dipole interactions, allylic 1,3-strain (A(1. 3) strain), allylic 1,2-strain (A(1.2) strain), and coulombic interact ions is discussed based on stereoselectivities observed with (alkoxyca rbonyl)-, cyano-, and aryl-substituted (arylsulfinyl)methyl radicals. In the second part, the effect of solvents and Lewis acids on the ster eoselectivity of reactions of (arylsulfinyl)- and (alkylsulfinyl)benzy l radicals has been examined.