Pyrene-dione

Koeber, R., Bayona, J. M., and Niesser, R., Determination of benzo[a]pyrene diones in air particulate matter with hquid chromatography mass spectrometry. Environ. Sci. Technol., 33, 1552-1558, 1999. 

In a solution containing oxygen, photolysis yields a mixture of 6,12-, 1,6-, and 3,6-diones. Nitration by nitrogen dioxide forms 6-nitro-, 1-nitro-, and 3-nitrobenzo[a]pyrene. When benzo [a] pyrene in methanol (1 g/L) was irradiated at 254 nm in a quartz flask for 1 h, the solution turned pale yellow. After 2 h, the solution turned yellow and back to clear after 4 h of irradiation. After 4 h, 99.67% of benzo[a]pyrene was converted to polar compounds. One of these compounds was identified as a methoxylated benzo[a]pyrene (Lu et al, 1977). A carbon dioxide yield of 26.5% was achieved when benzo [a] pyrene adsorbed on silica gel was irradiated with light (A, >290 nm) for 17 h (Freitag et al, 1985). 

Crystalline, solid, prisms, or plates. Benzo[e]pyrene is sensitive to ultraviolet light and may degrade into diones. 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

Peroxyacyl nitrates, see Acetaldehyde, Butane, 2-Bntanone, 2,3-Dimethylbntane Peroxybenzoic acid, see Toluene Peroxynitric acid, see Formaldehyde Peroxypropionyl nitrate, see 2-Methylpentane, Pentane Phenanthrene, see Anthracene, Bis(2-ethylhexyl) phthalate, Naphthalene Phenanthrene-9,10-dione, see Phenanthrene 9,10-Phenanthrenequinone, see Phenanthrene 4-Phenanthroic acid, see Pyrene... 

Triazolo-diazocine 12 was obtained through a [6+2] cycloaddition of cycloocta-l,3-dione and 4-pyren-l-yl-l,2,4-triazole-3,5-dione 80. Such a triazole derivative was obtained by in situ oxidation of l,2,4-triazolidine-3,5-dione 81, which was in turn obtained by reacting isocyanates and semicarbazides, followed by base-catalyzed cyclization... 

Mol. wt. 204.18, m.p. 296°. The reagent was prepared by condensation of cyclohexane-1,4-dione with malononitrile, bromination, and dehydrobromination with pyridine. The compound has properties similar to those of tetracyanoethylene and is a TT-acid of comparable strength. The equilibrium constant for ir-complex formation with pyrene is 78.4 as compared to 29.5 for the tetracyanoethylene-pyreno complex. 

In water, ozonation is generally slower and less efficient than chlorination in degrading PAHs (Neff 1979). Reaction pathways for ozonation of some PAHs include benz[a]anthracene to 7,12-quinone benzo[a]pyrene to 3,6-, 1,6-, and 4.5-diones and fluorene to fluorenone (NAS 1972). 

Park, J.H., Mangal, D., Frey, A.)., Harvey, R.G., Blair, I.A., and Penning, T.M. (2009) Aryl hydrocarbon receptor facilitates DNA strand breaks and 8-oxo-2 -deoxyguanosine formation by the aldo-keto reductase product benzo[o] pyrene-7,8-dione. J. Biol. Chem., 284, 29725-29734. 

Resistomycin. 3,5,7.HPTetrahydroxy-l,1.9-tri-methyl-2H-benzo[cd]pyrene-2,6(lH)-dione X -340. 

Ozonation of benzo[r,s,t]pentaphene (7) followed by oxidative workup led to benzo[r,s,t]pentaphene-5,8-dione (12) (14%), phthalic acid (13) (4%), p-terphenyl-2,2, 3, 2"-tetra-carboxylic acid-2, 3 -anhydride (14) (10%), and 2-(o-car-boxyphenyl)- ,10-phenanthrenedicarboxylic acid anhydride (15) (3%), with a 56% recovery of unreacted 7, Ozonation of pentaphene (11) led to a peroxidic mixture which on oxidative workup led to 2,2 -binaphthyl-3,3 -dicarboxalde-hyde (16) (16%), 2,2 -binaphthyl-3,3 -dicarboxylic acid (17) (16%), and 13 (2%), with a 28% recovery of unreacted 11. A comparison of the reactivity to ozone of carcinogenic polycyclic aromatics benzo c]phenanthrene (1), 7,12-di-methylbenz [a] anthracene (2), 3-methylcholanthrene (3), dibenz[si,]] - (4), and dibenzlsi, ]anthracene (5), benzo Si -pyrene (6) and 7, and the noncarcinogen 11, all determined in our laboratory, leads us to conclude that there is no simple, consistent correlation between carcinogenicity, K-and L-region additivity towards ozone and the Pullmans electronic theory of carcinogenesis. 

PET is the key feature of many other photo-oxidations involving aromatic substrates. It has been shown, for example, that pyrene and anthracene which are covalently attached to silica, gold or indium-doped tin oxide (ITO), undergo a photo-oxidation forming dihydroxy/dione derivatives. The reaction involves 02, formed by ET between excited pyrene, or anthracene, and O2, and it is suggested that the implications of such a photodegradation need to be considered when polycyclic aromatic hydrocarbons (PAHs) are used as spectroscopic probes in surface adlayers. The redox photosensitized amination of 1,2-benzo-1,3-cycloalkadienes, arylcyclopropanes, and quadricyclane with ammonia and primary amines, using 1,2,4-triphenylbenzene (1,2,4-TPB) or 2,2 -methylenedioxy-1,1 -binaphthalene in the presence of m- or p-dicyano-benzene (DCB), has been described (Scheme 51). The process involves the formation of the radical cation of 1,2,4-TPB, for example, by PET to the DCB, followed by hole transfer from the radical cation to the substrate, the latter... 

Dibenzoparathiazine. See Phenothiazine Dibenzopyran, tricyclic. See Xanthene Dibenzo (a,b) pyrene-7,14-dione 2,3,7,8-Dibenzopyrene-1,6-quinone. See Vat yellow 4 2,3,5,6-Dibenzopyridine Dibenzo (b,c) pyridine Dibenzo (b,e) pyridine. See Acridine Dibenzopyrrole. SeeCarbazole Dibenzosuberan-5-one. See Dibenzosuberone Dibenzosuberone... 

Benz (a I anthracene 5,6-oxide Benzo[a]pyrene 4,5-oxide (326) (3aa,4/6,7,6,7aa)-Hexahydro-3a.7a-dimethyl-4,7-epoxyisobenzofuran-1,3-dione (Cantharidin)... 

W-lndene-1,3(2H5-dione 1W-lndene-1,2,3-trione monohydrate lndeno[1,2,3-cd]pyrene... 

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