105864-92-4Relevant academic research and scientific papers
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.
Kinetic Evidence for Direct Electron Transfer between Tris(4-bromophenyl)ammoniumyl and the Acetate Anion in Acetonitrile Solution
Compton, Richard G.,Laing, Mark E.
, p. 1320 - 1321 (2007/10/02)
The reaction between tris(4-bromophenyl)ammoniumyl, electrogenerated from the parent amine, and the acetate anion has been studied in acetonitrile solution using rotating disc voltammetry and shown to involve a direct electron transfer reaction, resulting in an EC' mechanism, in contrast to a previously reported suggestion that acylation of the radical cation was the dominant reaction pathway under these conditions.
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.
Electron Transfer Reactions in Organic Chemistry. IX. Acyoxylation and/or Debromodimerization Instead of Electron Transfer in the Reaction between Tris(4-bromophenyl)ammoniumyl and Aliphatic Carboxylates
Eberson, Lennart,Larsson, Berit
, p. 210 - 225 (2007/10/02)
The reaction between tris(4-bromophenyl)ammoniumyl tetrafluoroborate and carboxylate ions (acetate, pelargonate and t-butylcyanoacetate), in the form of their hydrogen dicarboxylate salts, was studied in acetonitrile by product and kinetic analysis.Contrary to an earlier proposal, single electron transfer is not observed.Instead, acyloxylation of the aryl group(s) is the preferred reaction mode around room temperature, whereas around 0 deg C, a competing process, debromodimerization of tris(4-bromophenyl)ammoniumyl, takes over.The latter reaction was not observed in dichloromethane.The mechanistic consequences of these findings for other applications of triarylammoniumyls as mediators and catalysts are briefly discussed.Also chloride ion reacted with tris(4-bromophenyl)ammoniumyl to give oxidative substitution products.
