Naphthacene benzo

Scheme 44. Sulphonylphthalide condensation with enone 172 to construct a benzo[ ]naphthacene-8,13-dione 173 [126]...

These are benzo[cjphenanthrene and benz[ajanthracene which, as Hewett (36) noted in 1940, are both phenanthrene derivatives. In contrast, linear structures such as naphthacene are not associated... 

Figure 5.12 Polyaromatic hydrocarbon species (1) phenanthrene, (2) anthracene, (3) pyrene, (4) benz[o]anthracene, (5) chrysene, (6) naphthacene, (7) benzo[c]phenanthrene, (8) benzo[ghi] fluoranthene, (9) dibenzo[c,g]phenanthrene, (10) benzo[g/ ]perylene, (11) triphenylene, (12) o-terphenyl, (13) m-terphenyl, (14) p-terphenyl, (15) benzo[o]pyrene, (16) tetrabenzonaphthalene, (17) phenanthro[3,4-c]phenanthrene, (18) coronene...

Fig. 14 Reduction of PhjCSPh by electrochemically generated aromatic anion radicals (in DMF at 25°C). Variation of the rate-determining step rate constant, A , with the standard potential of the aromatic anion radical, p,g (from left to right azobenzene, benzo[c]cinnoline, 4-dimethylaminoazobenzene, terephthalonitrile, naphthacene, phlhalonitrile, perylene, fluoranthene, 9,10-diphenylanthracene). The dotted lines are the theoretical limiting behaviours corresponding to the concerted (right) and stepwise (left) pathways. (Adapted from Severin et al 1988.)...

Note Technical grades of naphthalene may contain one or more of the following impurities acenaphthene, benzo[6]thiophene, carbazole, chrysene, fluoranthene, fluorene, naphthacene, phenanthrene, pyrene, pyridine, and tetrazene. 

In the work of Hauser and Carnigal [126], which led to revisal of the structures of G-2N and G-2A, condensation using a sulphonylphthalide and the enone 172 (see Scheme 44) followed by air oxidation of the primary adduct in DMF at 100°C were used to construct the benzo[a]naphthacene-8,13-dione 173. 

The reaction between Fe3(CO)i2 and naphthacene lead to a new type of binuclear complex (CieHi2)[Fe2(CO)e] for which structure (XXIII) was proposed 22). The condensed aromatics acridine, phenazine, 4-benz[c]acridine, 5-benzo[a]phenazine, and dibenzo[a,c]phenazine were shown to react with Fe3(CO)ia to give complexes in which an Fe(CO)3 moiety is bound to a terminal ring directly adjacent to the heterocycle ring 22). 

Benzene is a major component in PVC pyrolysis. Other aromatic components also are present- In addition to the compounds indicated in Table 6.3.2, heavier aromatic compounds such as naphthacene and benzo[b]phenanthrene were indicated in PVC pyrolysates [23], Also, a more complete list of aromatic compounds generated in pyrolysis during non-flaming burning of PVC is reported in literature [24], Compounds with two, three, four aromatic cycles and even benzo[ghi]perylene (six cycles) are included in this list. 

Pentacene. Benzo[i>]naphthacene 2,3,6,7-diben-zoanthracene iin-naphthoanthracene, CnHM mot wt 278,35. C 94.93% H 5,07%. Synthesis from m-xylene or from 4-benzyl-1,3-dimethylbenzene and benzoyl chloride in presence of aluminum chloride or from terephthalyl chloride and o-tolylmagaesium bromide Oar, John, Ber, 62, 940 (1929) 63, 2967 (1930) 64, 981 (1931). Synthesis by reduction of 6,13-pentacenequinone Bruckner etal. Tetrahedron Letters 1960, no. 1,5 Bruckner, Tomas z. Acta Chim. Acad. Sci Hung. 28(4), 405 (196l). Structure Campbell et al, Acta Cryst. 14, 705 (1961). 

Naphthalene (1), anthracene (2), and naphthacene (4) constitute an homologous series in which each successive member is formed by benzo-fiision to the [b] side of the preceding member. As with other homologous series [5S], a plot of the gaseous enthalpies of formation of these species vs. the number of carbon atoms... 

In principle, one can represent the dibenzo[a,c]naphthacene (20) as a combination of anthracene and phenanthrene (23). In the same sense, di-benzo[a,c]phenazine (15) and tribenzo[a,c,i]phenazine (12) can be considered as quinoxaline-phenanthrene and benzo[g]quinoxaline-phenanthrene, respectively (Figure 9). The XH spectra of dianions 12, 15, and 20 are shown... 

Synthesis. The ketones used in the syntheses were 1-phenalenone (Aldrich), 7H-benz[de]anthracen-7-one (Phaltz and Bauer), 6H-benzo[de]pyren-6-one (W. Schmidt, Biochemical Institute for Environmental Carcinogens, Ahrensburg, West Germany), and 6H-benzo[/g]naphthacen-6-one (W. Schmidt). The ketone structures are shown in Chart I. 

The number of possible structures (Table 3.2) of polycyclic aromatic hydrocarbons increases with the total number of six-membered rings. For a molecule like pyrene, which is formed from four rings, six other ring arrangements are possible (Figure 3.15), leading to the compounds naphthacene, benz[a]anthracene, chrysene, benzo[c]phenanthrene, triphenylene, pyrene and benzo[a]phenalenyl. 

Coverage ( tmol/m ) Naphthacene Chrysene B enz [fl] -anthracene Benzo[c] pyrene... 

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