79642-79-8Relevant articles and documents
Mono-, Bis- and Trishydrazo, and -azo Compounds in the Tricyanobenzene Series, I. - Synthesis and Properties of the Title Compounds
Rieser, Juergen,Ismail, Nabila,Abou-Elenien, Gouda,Wallenfels, Kurt
, p. 1586 - 1597 (2007/10/02)
In 2-bromo-1,3,5-benzenetricarbonitrile (3) and chlorobenzenepentacarbonitrile (4) the halogen atoms can easily be substituted for phenylhydrazine.Also in 2,4,6-trichloro-1,3,5-benzenetricarbonitrile (1) and 2,4,6-trifluoro-1,3,5-benzenecarbonitrile (2) one or two halogen atoms can easily be replaced with phenylhydrazine forming the monohydrazo compounds 5a, b and the bishydrazo compounds 6a, b.The substitution of all three halogen atoms by phenylhydrazine is only possible under drastic conditions (pressure) using the fluorine compound 2.In 6a the remaining fluorine atom can also be replaced with phenolate ions, alkyl-(aryl)-thiolate ions or amines.Oxidation of the hydrazo derivatives 5a- d, 6a- f, and 7 with lead dioxide gives the azo compounds 8a-d, 9a-f; and 10.The chemical and spectroscopical properties of the hydrazo and azo compounds are described.