Regioselectivity and reactivity in the addition of trichloromethyl radicals to amides of unsaturated carboxylic acids

The AM1 method was used to analyze the factors that correlate with regioselectivity in the addition of radicals to 1,2-disubstituted unsaturated compounds. The rate constants of the addition of^.CCl₃ radicals to RCH=CHC(O)X (R = Ph, Me; X = N-pyrrolidyl) were determined by ESR. The analysis of the spin density distribution in mono- and 1,2-disubstituted alkenes and the experimental values for the rate constants of the addition of^.CCl₃ radicals to these alkenes allowed the authors to conclude that the efficiency of the addition of^.CC1₃ to unsaturated compounds depends only on steric effects.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 452–455, March, 1995.