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Arenediazonium o ‐Benzenedisulfonimides: Some Kinetics of Azo Coupling Reactions with Naphthols
Author(s) -
Boga Carla,
Degani Jacopo,
Vecchio Erminia Del,
Fochi Rita,
Forlani Luciano,
Todesco Paolo E.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200211)2002:22<3837::aid-ejoc3837>3.0.co;2-x
Subject(s) - chemistry , azo coupling , nitrobenzene , diazonium compounds , reagent , azo compound , kinetics , nitro , coupling reaction , polymer chemistry , organic chemistry , photochemistry , medicinal chemistry , catalysis , physics , alkyl , quantum mechanics , polymer
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)