Reactivity and stability of arenediazonium ions

Abstract

The reactions of arenediazonium ions are among the oldest to be studied intensively by organic chemists. The discussion between A. Hantzsch and E. Bamberger in the period 1894-1912 concerning the structure of the products formed in the reactions of

Dediazoniations of Arenediazonium Ions in Homogeneous Solution. Part XIV. 15N‐CIDNP. Investigation of the reactions of diazonium ions in weakly alkaline aqueous solutions

“…At present, there are very few reliable data concerning products, catalysis, kinetics and mechanism of dediazoniations in these media. This is in contrast to the situation in organic solvents [2] where products and mechanisms have been identified, and 'H-and 13C-CIDNP. investigations carried out [3-51.…”

Dediazoniation of Arenediazonium Ions in Homogeneous Solution. Part XII. Solvent effects in competitive heterolytic and homolytic dediazoniations

“…A comparison of the products of the 4 substituted benzenediazonium salts also makes it clear that an increase in the electrophilicity of the diazonium ion favours homolytic dediazoniations in borderline solvents. On the other hand, as shown previously [32], there is no observable correlation between the electrophilicity of solvents and the ease of homolytic dediazoniations. The same is true for 'classical' solvent parameters such as polarity or polarisability.…”

Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts

“…[51,52] www.chemeurj.org tion, do not need to be isolated. For example, a one-pot procedure allows the synthesis of azo compound 13 from methyl anthranilate (11) and allyl acetate (12). [51] Alternatively, when considered as more convenient, the arenediazonium ions can be added to the reaction mixture as storable tetrafluoroborate salts.…”

“…[8] Methods to initiate the dissociation of arenediazonium salts to aryl radicals and nitrogen by the reductive formation of an aryl diazenyl radical are numerous and have nicely been reviewed by Galli. [9] Based on the pioneering work by Walters, [10] Zollinger [11] and Cohen, [12] EPR and spin-trapping studies were later used to identify radical intermediates in diazonium salt reactions. [13] Among the synthetic equivalents of diazonium salts, aryltri-A C H T U N G T R E N N U N G azenes [14] and arylhydrazines [15] are the most prominent.…”