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Synthesis and reactions of N-(azulen-1-ylmethylene)arylamines

Domenii publicaţii > Chimie + Tipuri publicaţii > Articol în revistã ştiinţificã

Autori: A. C. Razus; C. Nitu; S. Carvaci; L. Birzan; S. A. Razus; M. Pop; L. Tarko

Editorial: J. Chem. Soc., Perkin Trans. 1, p.1227-33, 2001.


N-(Azulen-1-ylmethylene)arylamines were obtained in a fast quantitative convesion and high yield from the condensation of the corresponding azulene-1-carbaldehydes with aromatic amines without solvent. The reactions of the Schiff bases obtained were compared with those of the corresponding azo compounds which have already been studied. The lack of regioselectivity in the oxidation of imines with anhydrous ferric chloride at both the azulenyl and the aryl moiety in the contrast with the oxidation of coreponding azo compounds wich react mainly to aryl, is in agreement with the differences of the calculated Fukui one electron reactivity index Ir2 for the reactive positions in these molecules. from the calculated net charges for different positions in the molecules, a regioselective course for the electrophilic halogenation with cupric chloride for both imine and azo compounds at azulenic C3 position can be foreseen. However, the Schiff bases were chlorinated also at the aromatic ring; an explanation was proposed for this behaviour.

Cuvinte cheie: halogenare, imine, azulene // halogenation, imines, azulenes