117985-07-6Relevant articles and documents
Recoupling of 4-Arylazo-2-pyrazoline-5-ones with p-Quinonediimine Cations
Fanghaenel, E.,Akhlaq, M. S.,Grossmann, N.,Willscher, U.
, p. 275 - 283 (2007/10/02)
4-Arylazo-2-pyrazoline-5-ones (1a-j) readily undergo coupling reaction with p-quinonediimine cations (2a,b) to form azomethin dyes (3a,b).The dependence of the rate constants kK of the dye formation on the substituents of 1a-j as well as on the ionic strength show that the rate-determining step of the coupling reaction is the formation of the intermediate 4 in a bimolecular reaction between the carbanions of 1a-j and p-quinonediimine (2a,b).It became evident that the benzenediazoniumion (5a-j) is eliminated in the reaction of 4 to 3a, b.Under the coupling conditions used, substituted benzene is formed in the reduction reaction of 5a, b by the p-phenylendiamine (7a, b) or by the leuco dye (6a, b).