Origin of the Stereoselectivity in (Ethoxycarbonyl)??, Cyano??, and Phenyl??Substituted (Arylsulfinyl) methyl Radicals

P Renaud, T Bourquard, PA Carrupt…

Index: Renaud, Philippe; Bourquard, Thierry; Carrupt, Pierre-Alain; Gerster, Michele Helvetica Chimica Acta, 1998 , vol. 81, # 6 p. 1048 - 1063

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Citation Number: 16

Abstract

Abstract An explanation for the very high diastereoselectivity observed for the reactions of carbonyl-substituted (arylsulfinyl) methyl radicals is presented, 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 interactions is discussed based on stereoselectivities observed with (alkoxycarbonyl)-, cyano-, and aryl- ...

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