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The Electrochemical Oxidation of 4-Bromoaniline, 2,4-Dibromoaniline, 2,4,6-Tribromoaniline and 4-Iodoaniline in Acetonitrile Solution by Mihály Kádár; Zoltán Nagy; Tamás Karancsi; György Farsang is a Engineering article available to read on EtoBox.

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The electrochemical oxidation of 4-bromo-, 2,4-dibromo-, 2,4,6-tribromo-and 4-iodoanilines was investigated in acetonitrile solution. Based on the experimental results, it can be stated that the Bacon-Adams mechanism (J. Am. Chem. Soc. 90 (1968) 6596) is the main electrochemical oxidation route in acetonitrile solution similar to the 4-chloroanilines. In the cases of 4-bromo-and 2,4-dibromoanilines, the substituent in the para position eliminated in the dimerisation step, following its oxidation to bromine, which quantitatively substitutes the free ortho position of the starting bromoaniline. As a consequence of this, oxidised form of brominated 4-amino-diphenylamines is formed besides brominated anilines. Halogenisation did not take place at the oxidation of 2,4,6-tribromo-and 4-iodoaniline because the rejected halide ion can only be oxidised to elemental halogen (bromine and iodine). In the case of all bromo monomer compounds, the role of 'head-to-head' coupling was found negligible (azobenzene type compounds). 4,4%-Diiodo-azobenzene has been observed as by-product in traces at 4-iodoaniline oxidation. The electrochemical oxidation of 4-bromoaniline resulted in the 'ortho-couplin

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Author

Mihály Kádár; Zoltán Nagy; Tamás Karancsi; György Farsang

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0013-4686)

Published

2001

Language

EN

Field

Engineering (Physical Sciences)