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Origin of the stereoselectivity in (ethoxycarbonyl)-, cyano-, and phenyl-substituted (arylsulfinyl)methyl radicals

Renaud, P.
Bourquard, T.
Gerster, M.
Published in Helvetica chimica acta. 1998, vol. 81, no. 6, p. 1048-1063
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-substituted (arylsulfinyl)methyl radicals. In the second part, the effect of solvents and Lewis acids on the stereoselectivity of reactions of (arylsulfinyl)- and (alkylsulfinyl)benzyl radicals has been examined
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RENAUD, P. et al. Origin of the stereoselectivity in (ethoxycarbonyl)-, cyano-, and phenyl-substituted (arylsulfinyl)methyl radicals. In: Helvetica chimica acta, 1998, vol. 81, n° 6, p. 1048-1063. doi: 10.1002/hlca.19980810518

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Deposited on : 2010-08-06

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