1,3-DipoIare Cycloaddition von Dinitronen - Bildung tricyclischer Dimerer / 1,3 -Dipolar Cycloaddition of Dinitrones - Formation of Tricyclic Dimers

Hans Günter Aurich, Abdellatif Chair
1994 Zeitschrift für Naturforschung. B, A journal of chemical sciences  
Various dialdehydes (1 -5) were formed by addition of dithiols to acrolein. Reaction of these dialdehydes with N-alkylhydroxylamines afforded dinitrones the two nitrone groups of which were joined by an alkylidene chain containing two sulfur atoms (6a,b-10a,b). Cycloaddition of these dinitrones with dimethyl acetylenedicarboxylate proceeded in the usual way giving bis(4-isoxazolines) (11a-15a). However, analogous dinitrones formed by reaction of the dialdehydes with N-(4-tert-butylphenyl)
more » ... -butylphenyl) hydroxylamine could not be isolated. Instead tricyclic compounds arose in which the central macrocyclic ring is flanked by two isoxazolidine rings (16c-20c). Obviously, the dinitrones formed as intermediates underwent dimerization with formation of the tricyclic compounds by cycloaddition between two nitrone groups and two tautomeric N-hydroxyenamine moieties. Two of the tricyclic compounds (16c and 20c) formed 1:1 complexes with NiCl2 and FeCl3, respectively.
doi:10.1515/znb-1994-0719 fatcat:j7kjtva5t5gvhhyrwck7jjgzey