The electrochemical oxidation of polyfluoroaromatic amines—II

Anodic Oxidation of N,N,N'-Triphenyl-o-Phenylenediamine

“…Interestingly, this reaction does not occur with 2aminodiphenylamine (N-phenyl-o-phenylenediamine) (9,11), although it has been noted for a series of polyfluorinated 2-aminodiphenylamines (12,13). It was noted in these latter systems that a necessary condition for cyclization was a fluorine ortho to the NH group in the ring not containing the amino function (12); the dihydrophenazine derivatives were oxidized on to the corresponding phenazines since the nitrogens were not protected.…”

“…In addition, a number of papers have been published describing the effect of electrolysis of blood and plasma in both in vitro and in vivo systems. While the work of our group and of several other workers gives evidence for the accelerated coagulation of electrolyzed plasma or blood (7)(8)(9)(10)(11)(12)(13), there are other authors who have presented work which gives somewhat conflicting results (14)(15)(16)). Blood as well as plasma are far too complex systems to investigate the electrochemical phenomena taking place in the over-all thrombosis reaction, or in general in blood coagulation.…”

Preparation of Halogenated Fluorescent Diaminophenazine Building Blocks

“…The most popular route is based on direct condensation of adequately functionalized o -quinone or catechol with o -phenylenediamine derivatives. − This method permits the preparation of a variety of extended polyazaacene cores in modest to high yields from readily available starting materials. Other methods feature the intramolecular cyclization of substituted diphenylamines such as 2,2′-diaminodiphenylamines and 2-aminodiphenylamines, , 2-nitrodiphenylamines, or 2-fluoro-2′-nitrodiphenylamines; the Pd-catalyzed cyclization of 2-amino-2′-bromodiphenylamines; the chemical − or electrochemical − oxidative cyclization of fluorinated aniline derivatives; and the oxidative condensation of o -phenylenediamines. , We investigate the latter strategy and present an expeditious protocol for the synthesis of 7,8-dihalo-2,3-diaminophenazines, where the halogen substituents can be F, Cl, or Br.…”

Polyfluoroaromatic Compounds

“…These have been formulated as radical substitutions [176,177] (Figure 9.74). These have been formulated as radical substitutions [176,177] (Figure 9.74).…”