Electron Transfer Reactions in Organic Chemistry. XII. Reactions of 4-Substituted Triarylaminium Radical Cations with Nucleophiles; Polar vs. Electron Transfer Pathways.

Abstract

The reactions between tris(4-bromophenyl)aminium ion and Cl-, Br-, I- and CN- have been investigated. Cl- and CN- reacted to give the product of substitution (in the 2-position), whereas Br- and I- underwent electron transfer oxidn. with formation of tribromide and triiodide ion, resp. A kinetic study gave results consistent with those obtained by other authors for reactions between (9,10-diphenylanthracene).bul.+ and the same nucleophiles, but not with those published for (perylene).bul.+/nucleophile reactions.