210539-74-5Relevant academic research and scientific papers
Origin of the Stereoselectivity in (Ethoxycarbonyl)-, Cyano-, and Phenyl-Substituted (Arylsulfinyl)methyl Radicals
Renaud, Philippe,Bourquard, Thierry,Carrupt, Pierre-Alain,Gerster, Michèle
, p. 1048 - 1063 (1998)
An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfmyl)methyl radicals is presented, based on experimental results and semiempirical calculations. The influence of dipole-dipole interactions, allylic 1,3-strain(A1,3 strain), allylic 1,2-strain (A1,3 strain), and coulombic interactions is discussed based on stereoselectivities observed with (alkoxycarbonyl)-, cyano-, and aryl-substituted (arylsulfinyl)methyl radicals. In the second part, the effect of solvents and Lewis acids on the stereoselectivity of. reactions of (arylsulfmyl)- and (alkylsulfinyl)benzyl radicals has been examined.
