On the chemistry of iodonyl radicals. The oxidation of iodobenzene by t-butyl hypochlorite

Abstract

The reaction of iodobenzene with t-butyl hypochlorite proceeds by a free radical chain mechanism, forming as the sole product iodobenzene t-butoxy chloride (IBBC). The photoinduced or thermally induced reactions of IBBC with hydrocarbon substrates yield chlorinated hydrocarbons by a radical chain halogenation sequence involving t-butoxyiodonyl benzene as the principal chain-carrying species. The photolysis or thermolysis of IBBC in the absence of molecular oxygen yields products resulting from a variety of free radical chain reactions, while thermolysis in the presence of oxygen yields only iodobenzene and t-butyl hypochlorite.