ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electrochemical Oxidation of Organic Compounds in Fluorosulfuric Acid. V. Anodic Behaviour of Aromatic Nitrocompounds, Nitriles, Amines, Acetamides, and OximesThe anodic behaviour of a series of methyl substituted nitrobenzenes, benzonitriles, aniline derivatives, acetanilides and acetophenone oximes was investigated by cyclic voltammetry at platinum electrodes in HSO3F at -76°C. With the exception of the parent compounds and partly of the monomethyl derivatives relatively stable cation radicals could be detected. In a second anodic wave in many cases the functionalization of a CH3-group to CH2-OSO2F took place. From a comparison of the peak potentials and from the dependence of the voltammetric curves on the scan rate follows that the aniline derivatives are oxidized without deprotonation of the -NH3+ group, whereas for the nitrocompounds, nitriles and acetanilides a deprotonation of the functional group is coupled with the oxidation, and the cation radicals are stable onyl in the deprotonated state. A kinetic study of the subsequent reaction of some nitrocompounds was made and the deviating behavior of some acetanilides was found to be due to the anodic dimerization to benzidine derivatives.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19833250411
