69625-10-1Relevant articles and documents
Transformations of Diazonium Salts. III. Transformations, Acid-Base Properties, and Reactivity of Nitronaphthyldiazonium Salts
Bagal,Luchkevich,El'tsov
, p. 119 - 132 (2007/10/03)
The transformations in water-alkali media, stability, acid-base properties, and activity in azocoupling of a series of nitronaphthaleneldiazonium salts are studied by preparative, spectroscopic, and kinetic methods. 4-Nitronaphthaleneldiazonium cation shows the highest acidity and the highest activity in azo-coupling. Nitro substitution in other positions much less affects the reactivity of the naphthaleneldiazonium cation. Unlike nitro derivatives of benzene series of diazo compounds, their naphthalene analogs show no effect of isomerism of diazotate anions, other conditions being equal. The experimental evidence does not allows unabiguous assignment of the ntronaphthalene diazotates to Z or E series. The transformations of nitronaphthalenediazonium salts involve addition of hydroxide anion to the ring carbon atom, which results in accumulation of the structural isomer of diazohydroxide. It is assumed that an analogous addition product arises in reaction of the diazonium cation with an azo component, and being an electrophilic species it is capable to enter azo-coupling.
