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MECHANISMS OF FREE-RADICAL REACTIONS. XV. SELECTIVITY OF THE FREE-RADICAL CHLORINATION OF ALIPHATIC HYDROCARBONS BY ARYLCHLOROIODONIUM CHLORIDES
Dneprovskii, A. S.,Krainyuchenko, I. V.,Kasatochkin, A. N.
, p. 437 - 440 (2007/10/02)
The free-radical chlorination of 2,3-dimethylbutane, 2,2,4-trimethylpentane, adamantane, and cyclohexane by arylchloroiodonium chlorides was investigated by the method of competing reactions.It was shown that the introduction of electron-withdrawing substituents into the arylchloroiodonium chloride leads to an increase in the sensitivity of the process to the polar effect of the substituents in the substrate and to a decrease of the selectivity toward variation in the dissociation energy of the C - H bond.The importance of steric effects in the reaction was noted.
