Investigation of the stereochemistry of the radical telomerization of propylene with 1,1,1,3-tetrachlorobutane by the method of conformational PMR analysis

Abstract

1. The stereochemistry of the radical telomerization of propylene by 1,1,1,3-tetrachlorobutane, catalyzed by Fe(CO)5 with additions of i-C3H7OH or dimethylformamide at 95°, was investigated by the method of conformational PME analysis. 2. To evaluate the diastereomeric composition of the lower member of the telomer homolog series of 2,4,4,6-tetrachloroheptane, we studied the distribution of the rotational isomers of the molecule in several solvents of different types and assigned the configurations of two racemic forms, on the basis of a comparison of the conformational composition and differences in shielding constants of the methylene protons. 3. A total lack of stereodirection of the substitution reaction with the participation of the intermediate acyclic radical, probably determined by the absence of induction of the asymmetrical atom at a 1,5-distance from the reaction center, was detected.