Acephenanthrylene

Considerable attention has been directed to the formation of nitroarenes that may be formed by several mechanisms (a) initial reaction with hydroxyl radicals followed by reactions with nitrate radicals or NO2 and (b) direct reaction with nitrate radicals. The first is important for arenes in the troposphere, whereas the second is a thermal reaction that occurs during combustion of arenes. The kinetics of formation of nitroarenes by gas-phase reaction with N2O5 has been examined for naphthalene (Pitts et al. 1985a) and methylnaphthalenes (Zielinska et al. 1989) biphenyl (Atkinson et al. 1987b,c) acephenanthrylene (Zielinska et al. 1988) and for adsorbed pyrene (Pitts et al. 1985b). Both... 

Zielinska B, J Arey, R Atkinson, PA McElroy (1988) Nitration of acephenanthrylene under simulated atmospheric conditions and in solution and the presence of nitroacephenanthrylenes in ambient particles. Environ Sci Technol 22 1044-1048. 

Synonyms Benz[e]acephenanthrylene 3,4-Benz[e]acephenanthrylene 2,3-Benzfluoranthene 3,4-Benzfluoranthene Benzo[e]fluoranthene 2,3-Benzofluoranthene 3,4-Benzofluoranthene 3,4-Benzo[ ]fluoranthene B(6)F BRN t872553 CCRtS 72 NSC 89365. 

A particularly interesting group of compounds in combustion effluents are those with a vinylic bridge such as acenaphthylene (peak 4) and cyclopenteno[cd]pyrene (peak 32). Peak 23, although not labeled, has been positively identified as acephenanthrylene, a compound which also has a vinylic bridge. We emphasize this structural feature because of its chemical reactivity (compared to the fully aromatic portions of the PAH). We shall see later that this reactivity is important when considering the fate of PAH in the atmosphere. 

Zielinska, B., J. Arey, R. Atkinson, and P. A. McElroy, Nitration of Acephenanthrylene under Simulated Atmospheric Conditions and in Solution and the Presence of Nitroacephenanthrylene(s) in Ambient Particles, Environ. Sci. Technol., 22, 1044-1048 (1988a). 

Figure 2. Gas chromatogram of A, PAH fraction of diesel particulate extract (Sl-C2) and By its HPLC subfraction C (S1-C2). GC conditions 45- X 0.35-mm id SE54 glass capillary column flame ionization detector temperature, 110°C for 2 min, programmed to 170°C at 10°/min, to 212°C at 3°/min, to 278°C at 8°/min. Peak identities 1, phenanthrene 2, anthracene 3-6, methylanthracene/-phenan-threne 7, 2-phenylnaphthalene 8-10, dimethylanthracene/-phenanthrene 11, fluoranthene 12, aceanthrylene/acephenanthrylene 13, pyrene 14-15, trimethylan-thracene/-phenanthrene 16, benzo [ghi]fluoranthene 17, benzo[a/anthracene 18, triphenylene 19, chrysene 20, benzo[b]fluoranthene 21, benzo[]]fluoranthene ...

Scott, L. T. Roelofs, N. H. 1987 Benzene ring contractions at high temperatures. Evidence from the thermal interconversions of aceanthrylene, acephenanthrylene and fluoranthrene. J. Am. chem. Soc. 109, 5461-5465. 

A recent example of intermolecular photocycloaddition between acephenanthrylene demonstrates the role of 7i-stacking [26], The singlet excited state gives only the cis dimer that the authors suggest arises from an excimer state. The triplet excited state results in formation of both cis and trans cyclobutanes. Interestingly, in the presence of oxygen the cis dimer is the only product due to quenching of the triplet excited state. 

SYNS 3,4-BENZ(e)ACEPHENANTHRYLENE 2,3-BENZFLUORANTHENE 3,4-BENZFLUORANTHENE BENZO(b)FLUORANTHENE BENZO(e)FLUOR-ANTHENE 2,3-BENZOFLUORANTHENE 3,4-BENZOFLUORANTHENE 2,3-BENZOFLUOR-ANTHRENE B(b)F... 

BENZACENAPHTHENE see FDFOOO BENZ(e)ACEPHENANTHRYLENE see BAW250 3,4-BENZ(e)ACEPHENANTHRYLENE see BAW250 BENZACILLIN see BFC750 BENZACONINE see PIC250... 

The same cyclization also succeeds in the absence of a carboxylic group. Heating the fulvene (361), prepared by condensation of o-chlorobenzaldehyde with fluorene, with potassium hydroxide in boiling quinoline leads to benzo(e)acephenanthrylene (J62)127> ... 

The spectroscopic studies 83,84) afforded chemical applications. The reductive alkylation of dianion 82 gave alkylated products only in the periphery121K This observation confirms the structure So2 suggested by Rabinovitz and Hafner 84b). Contrary to the reductive alkylation of 232 the quench of dianion 82 did not afford any alkylated product at the central atom C-l 1. The alkylated acenaphthylene served as a starting material for the preparation of acephenanthrylene 34z (vide supra)121). 

The higher homologs of acenaphthylene dianion 82 are the aceanthrylene dianion 33 and acephenanthrylene dianion 34 122,123). The convenient synthesis of the the hydrocarbon enabled a detailed investigation of their metal reduction and the exploration of their patterns of delocalization. Despite their being (4n + 2)ji-electron systems, these anions are not diatropic as one may expect from counting their jc-electrons. 

Weyand EH, Amin S, Sodhi R, et al. 1991c. Effects of methyl substitution on the metabolism and binding of benz[e]acephenanthrylene. In Garriques P, Lamotte M, eds. Polycyclic aromatic compounds. Synthesis, properties, analytical measurements, occurence, and biological effects. Proceedings of the thirteenth international symposium on polynuclear aromatic hydrocarbons. Philadelphia, PA Gordon and Breach. 

Benz[e]acephenanthrylene 2,3-benzfluoranthene 3,4-benzfluoranthene 2,3-benzofluoranthene 3,4-benzof1uoranthene ... 

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