Kinetic investigation of azo coupling reactions between naphthols and 4-methoxy- and 4-nitrobenzenediazonium o- benzenedisulfonimides has been carried out for comparison with the related benzenediazonium tetrafluoroborates. The data clearly indicate that the two kinds of diazonium salts show very similar reactivities. This fact emphasizes that arenediazonium o-benzenedisulfonimides, which are very stable, may be used as alternatives to the more usual diazonium salts. The azo coupling reactions between 4-nitro-and 4-methoxybenzenediazonium salts and 1-bromo-2- naphthol, performed with equimolecular amounts of both reagents, showed the unexpected formation of large amounts of 1-bromo-4-nitrobenzene and 1-bromo-4-methoxybenzene. Some mechanistic implications of this behaviour are discussed. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Boga, C., Degani, J., Del Vecchio, E., Fochi, R., Forlani, L., Todesco, P.E. (2002). Arenediazonium o-benzenedisulfonimides: Some kinetics of azo coupling reactions with naphthols. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002(22), 3837-3843 [10.1002/1099-0690(200211)2002:22<3837::AID-EJOC3837>3.0.CO;2-X].
Arenediazonium o-benzenedisulfonimides: Some kinetics of azo coupling reactions with naphthols
Boga C.;Degani J.;Del Vecchio E.;Fochi R.;Todesco P. E.
2002
Abstract
Kinetic investigation of azo coupling reactions between naphthols and 4-methoxy- and 4-nitrobenzenediazonium o- benzenedisulfonimides has been carried out for comparison with the related benzenediazonium tetrafluoroborates. The data clearly indicate that the two kinds of diazonium salts show very similar reactivities. This fact emphasizes that arenediazonium o-benzenedisulfonimides, which are very stable, may be used as alternatives to the more usual diazonium salts. The azo coupling reactions between 4-nitro-and 4-methoxybenzenediazonium salts and 1-bromo-2- naphthol, performed with equimolecular amounts of both reagents, showed the unexpected formation of large amounts of 1-bromo-4-nitrobenzene and 1-bromo-4-methoxybenzene. Some mechanistic implications of this behaviour are discussed. © Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
