Intra- versus intermolecular electron transfer in radical nucleophilic aromatic substitution of dihalo(hetero)arenes - a tool for estimating π-conjugation in aromatic systems.

ABSTRACT: In this paper, the application of the double radical nucleophilic aromatic substitution (S_RN1) in various dihalogenated, mostly diiodinated, π-conjugated systems as a tool for qualitatively estimating their π-conjugation is described. This approach uses electron delocalisation as a measure of π-conjugation. Electron injection into the π-system is achieved via reaction of an intermediate aryl radical, itself generated from a dihalogenated π-system via SET-reduction of the C-I bond and subsequent reaction with a thiolate anion. The generated arene radical anion can then further react with the second aryl-halogen moiety within the π-system via an intramolecular electron transfer process. The efficiency of this intramolecular electron transfer is related to the

SUBMITTER: Janhsen B 

PROVIDER: S-EPMC5436300 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature