Polar and steric effects in hydrogen abstraction by dialkylamine cation radicals

Abstract

The high selectivity observed in the chlorination of methyl decanoate by N-chlorodialkylamines is due to the inductive effect of the methoxycarbonyl group and a (ω– 1) effect which seems to be steric. This second effect occurs also in the chlorination of n-heptane, in which the methylene at position 2 is more reactive than the others, and it is increased by use of an N-chlorodialkylamine with higher steric requirement.