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- ...
