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By Mellor J.W

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The kinetic behaviour for nitrosation of secondary aromatic amines is very similar to that of primary aromatic amines, and the rate constants for the reactions of aniline and N-methylaniline are very close together, implying, as is generally believed, that the first stage - rate limiting N-nitrosation - is the same in both. Again there is a tendency towards diffusion controlled reactions for the more basic amines with a number of reagents. The position with aliphatic secondary (and primary) amines is a little more puzzling in this regard.

Other modifications have included the diazotisation of 4-methylaniline and coupling with 2-naphthol-3,6-disulfonic acid. The first azo dyes to be produced commercially were derived from aniline derivatives, and colour changes were brought about by substituent group changes, both in the anilines and in the coupling reagents. The latter usually contained sulfonic acid groups in order to confer water solubility on the final dye. Later, the range was extended to include exocyclic heterocyclic primary amines, since many had better colour properties.

In this acid region Cnitrosation occurs, which may arise from a Fischer-Hepp rearrangement (see Chapter 3) of A r ^ H 2 N 0 . 3. Secondary amines Both aliphatic and aromatic secondary amines, R2NH, yield Nnitrosamines, Eq. (105), on nitrosation, using any of the conventional R2NH + HNO2 < " R2NNO + H2O (105) 44 Nitrosation Reactions and the Chemistry of Nitric Oxide nitrosating agents. The reaction is somewhat reversible, but much less so than is the reaction with alcohols, and the equilibrium position lies well over towards nitrosamine formation.

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