Glyoxal dihydrazone

Oxidation of bis-hydrazones of aliphatic polyfluorinated a-dicarbonyl compounds with S02C12 or bromine forms isomeric 1-amino-1,2,3-triazoles, one of which was identified by X-ray analysis (96JFC(79)45) (Scheme 86). Oxidation of polyfluoroalkyl-substituted glyoxal dihydrazones gives only one isomer. 

Figure 16.1. Schematic energy level diagram for glyoxal dihydrazone, glyoxalazine dihydrazone, and polyazine. The energy levels for the monomer and dimer are taken from the calculation in reference [18] while the band structure of the polymer is estimated from these results.

Crystal structures have been studied on two monomeric model compounds glyoxal dihydrazone (GDH) [9] and 2,3-butanedione dihydrazone (BDDH) [7]. The geometric parameters for these two materials are given in Table 16.1. GDH crystallizes in the monoclinic space group P2i/a and has cell parameters a = 7.744 A, b = 4.m A, c = 8.063 A, and ) = 115.66° while... 

Table 16.1 Bond lengths and bond angles for glyoxal dihydrazone (GDH) and 2,3-butanedione dihydr one (BDDH). The atomic numbering is shown below.

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