134. 3,3-Dialkyltriazenecarboxylic Derivatives by Oxidative Hydro-Acyl-Elimination from 3,3-Dialkyltriazane-1,2-dicarboxylic Derivatives

Article abstract of DOI:10.1002/hlca.19830660510

The preparation and some properties of esters and amides of 3,3-dialkyltriazenecarboxylic acids (6) are described.These novel triazenes 6 were obtained by treatment of diesters, diamides and ester-amides of 3,3-dialkyltriazane-1,2-dicarboxylic acids (3) with lead tetraacetate, when an elimination of the COOR- or the CONHR-group at N(2) together with the H-atom at N(1) took place.The precursor triazanes 3 were readily available from the addition of secondary amines 2 to diesters, diamides or ester-amides of diazenedicarboxylic acid (1).The spectral properties of the triazenes 6, including the 15N-NMR signals of one example, are compared with those of the triazanes 3.They express the structural features due to conjugation in 3,3-dialkyltriazenecarboxylic derivatives, including the resistance to rotation around the N(2), N(3)-bond.