105864-92-4Relevant articles and documents
The Reaction between Tris(4-bromophenyl)aminium Ion and Acetate Ion is an Electrophilic Reaction!
Eberson, Lennart,Olofsson, Berit
, p. 698 - 701 (2007/10/02)
A recent claim that the reaction between acetate ion and tris(4-bromophenyl)aminium ion (TBPA+.) is an electron transfer process, in contrast with the polar reaction demonstrated earlier between the hydrogendiacetate ion and TBPA+., is refuted.Product studies show that the possible products of electron transfer between acetate ion and TBPA+., methane and ethane, are formed in -3percent yield and that ring acetoxylation of TBPA, i. e., the polar process, is predominant.The demonstration of 'catalytic' electrochemical oxidation of TBPA/AcO- mixtures is shown to be the result of a multi-step oxidation mechanism, due to the small difference in redox potential of TBPA and its 2-acetoxy derivative, 0.09 V.
Electron Transfer Reactions in Organic Chemistry. XII. Reactions of 4-Substituted Triarylaminium Radical Cations with Nucleophiles; Polar vs. Electron Transfer Pathways
Eberson, Lennart,Larsson, Berit
, p. 367 - 378 (2007/10/02)
The reactions between tris(4-bromophenyl)aminium ion (TBPA+.) and chloride, bromide, iodide and cyanide ion have been investigated.Chloride and cyanide ion reacted to give the product of substitution (in the 2-position), whereas bromide and iodide underwent ET oxidation with formation of tribromide and triiodide ion, respectively.A kinetic study gave results consistent with those obtained by other authors for reactions between (9,10-diphenylanthracene)+. and the same nucleophiles, but not with those published for (perylene)+./nucleophile reactions.