N-methylcarbazole

Yang, W. and Davis, P.J. (1992) Microbial models of mammalian metabolism biotransformation of N-methylcarbazole using the fungus Cunninghamella echinulata. Drug Metabolism and Disposition The Biological Fate of Chemicals, 20, 58 46. 

Shen T, Hollenberg PF. The mechanism of stimulation of NADPH oxidation during the mechanism-based inactivation of cytochrome P450 2B1 by N-methylcarbazole redox cycling and DNA scission. Chem Res Toxicol 1994 7(2) 231-238. 

The formation of a small amount of naphthalene as a by-product of the reaction of benzyne with iV -methylpyrrole was noted by Wittig and Behnisch. Some related examples have recently been described. The tetrachloronaphthalen-l,4-imine (108) with benz5me gave N-methylcarbazole, which it is tempting to see as arising from the reaction of an intermediate zwitterion (compare 166) with another molecule of benzyne or, more likely, a benzyne precursor. The complementary product, 1,2,3,4-tetrachloronaphthalene, was not identified in this case. 

Preannihilative electrochemical oxidation of the phenanthrene anion has given a green emission13,64 spectrally nearly identical to the previously reported room-temperature phenanthrene phosphorescence which is a single broad peak.71 Chemical oxidation of the chrysene anion with Wurster s blue perchlorate produced an emission containing three bands at 19,800, 18,600, and 17,400 cm"1 which seem to correspond to the known phosphorescence bands of chrysene (19,500,18,500, and 16,600 cm-1). Chemical oxidation of the radical anion of N-methylcarbazole has possibly led to phosphorescent emission from this triarylamine.7... 

Diaryl amines, ethers or sulphides, or their aryl vinyl analogues, provide another 6-electron system related to stilbene, but for these a pair of electrons is provided by the single heteroatom (ArXAr or ArXC=C). With dtaryl compounds the initial photocydized product is a zwitterion that undergoes a proton shift to give, for example, N-methyl-4a,4b-dihydrocarbazole from methyldiphenylamine, with subsequent oxidation to N-methylcarbazole (3.74). With the aryl vinyl analogues the product after the proton shift can normally be isolated (3.751. An especially useful variation of this reaction employs... 

In some of the early experiments, organochlorine compounds were detected by fluorescence when the chromatogram was sprayed with N-methylcarbazole or rhoda-mine B C 1 33. Also, fluorescence whiteners (1 4) known as Calcofluors, were used to visualize carbamates, uracils, and ureas. Both of these techniques, however, were only of a semi-quantitative nature. 

Valence isomerisations of some norbomadienes have been photosensitised using N-methylcarbazole and evidence presented supports the view that single... 

Figure 1. UV-absorption spectra of PVCA and monomeric model N-methylcarbazole replotted after Schneider (17)...

Naphthalene is formed from the N-nitrosoimine 69 at 45°C via a cheletropic reaction.62 In some instances benzyne induces deamination of naphthalen-l,4-imines, since naphthalene was a by-product of the reaction of benzyne with N-methylpyrrole,63 and the naphthalene ester 79 is produced by reaction of 78 with benzyne.68 An indication of the fate of the extruded nitrogen-containing fragment is provided by the identification of N-methylcarbazole as a product of the reaction of 82 with benzyne. 

The effect of oxygen on the photocyclization of A-methyldiphenylamine to N-methylcarbazole in n-hexane, water, and aqueous surfactants has been studied by... 

Further studies of the photochemically induced conversion of JV-methyl-diphenylamine into N-methylcarbazole have been reported.28 Two successive intermediates have been detected, namely the amine triplet and iV-methyl-4a,4b-dihydrocarbazole. Oxygen appears to participate in the overall reaction in two ways, viz. by dehydrogenation of the dihydrocarbazole intermediate to carbazole and by quenching the amine triplet. Non-oxidative cyclization of 5-(iV-methyl-anilino)- and 5-(iV-acetylanilino)-l,3-dimethyluracil (26) similarly gives the trans-dihydropyrimido[5,4-6]indoles (27) in high yield.24 Orbital symmetry arguments... 

Additives used in final products Plasticizers N-methylcarbazole, N-ethylcarbazole, N-butyl-carbazole, N-hexylcarbazole, N-phenylcarbazole, 1,3-biscar-bazolylpropane, o-nitroanisole, m-nitroanisole, p-nitroanisole, triphenylamine Release amorphous silica, PVDF ... 

Ci3HiiBrN2, 2-Allyl-2-azonia-7-azabiphenylene bromide, 46B, 268 C13H11CIN2 2 H2O, 9-Aminoacridinium chloride dihydrate, 46B, 269 C13H11N, N-Methylcarbazole, 45B, 295... 

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