Benzo c phenanthrene

The series M(PP)C1 (PP = 2,ll-bis(diphenylphosphinomethyl)benzo[c]-phenanthrene M = Cu, Ag, Au) is interesting in showing group trends (Table 4.7) where the silver and copper complexes have trigonal coordination and the gold member is linear [50]. 

Methods for the synthesis of the biologically active dihydrodiol and diol epoxide metabolites of both carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons are reviewed. Four general synthetic routes to the trans-dihydrodiol precursors of the bay region anti and syn diol epoxide derivatives have been developed. Syntheses of the oxidized metabolites of the following hydrocarbons via these methods are described benzo(a)pyrene, benz(a)anthracene, benzo-(e)pyrene, dibenz(a,h)anthracene, triphenylene, phen-anthrene, anthracene, chrysene, benzo(c)phenanthrene, dibenzo(a,i)pyrene, dibenzo(a,h)pyrene, 7-methyl-benz(a)anthracene, 7,12-dimethylbenz(a)anthracene, 3-methylcholanthrene, 5-methylchrysene, fluoranthene, benzo(b)fluoranthene, benzo(j)fluoranthene, benzo(k)-fluoranthene, and dibenzo(a,e)fluoranthene. 

Benzo(c)phenanthrene (BcP) is exceptionally weak or inactive as a carcinogen in experimental animals (51). On the other hand, the bay region anti diol epoxide of BcP (14) exhibits high tumor initiating activity on mouse skin (65). 

The carcinogenicity of PAH with relativelyTigh IP, such as benzo[c]phenanthrene, benz[a]anthracene, chrysene, 5-methyl chrysene and dibenz[a,h]anthracene (Table I), can be related to the formation of bay-region diol epoxides catalyzed by monooxygenase enzymes (j>). However, the most potent carcinogenic PAH have IP < ca. 7.35 eV. 

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...

The EH-catalyzed hydration of the enantiomers of the K-region epoxides of BaA, CR, and BcPh allows informative comparisons to be made [92 - 94], With four among the six substrates, nucleophilic attack is selective for the oxirane C-atom with (5)-configuration (Fig. 10.12). This is, for example, true for the two enantiomers of chrysene 5,6-oxide. Looking at the data in another way, it is also apparent that, irrespective of the enantiomer, nucleophilic attack occurs preferentially at C(5) for benz[a]anthracene 5,6-oxide, but at C(6) for benzo[c]phenanthrene 5,6-oxide. In other words, the regio- and... 

Fig. 10.12. Upper part The K, M, bay, and fjord regions of three isomeric tetracyclic aromatic hydrocarbons (benz[a]anthracene (BaA, 10.31), chrysene (CR, 10.32), and benzo[c]phenanthrene (BcPh, 10.33)). Lower part. The three pairs of enantiomeric (S,R)- and (R,S)-K-region epoxides and...

A. Harsch, J. M. Sayer, D. M. Jerina, P. Vouros, HPLC-MS/MS Identification of the Positionally Isomeric Benzo[c]phenanthrene Diol Epoxide Adducts in Duplex DNA , Chem. Res. Toxicol. 2000, 13, 1342 - 1348. 

L. Lewis-Bevan, S. B. Little, J. R. Rabinowitz, Quantum Mechanical Studies of the Structure and Reactivities of the Diol Epoxides of Benzo[c]phenanthrene , Chem. Res. Toxicol. 1995, 8, 499 - 505. 

Fig. 18 Representative chrysenes, benzo[c]phenanthrenes, benzo[g]chrysene, and their carbocations and nitro-derivatives.

IV Benzo[c]chrysene, benzo[c]phenanthrene, benzole]pyrene, chrysene, coronene, dibenzanthracene, dibenzolc,/]pyrene... 

Figure 1. Gas chromatogram of PAH in a work atmosphere a, particulate PAH b, gaseous PAH. The peak identities are 1, naphthalene 2, 2-methylnaphthalene 3, 1 -methylnaphthalene 4, biphenyl 5, acenaphthene 6, dibenzofuran 7, fluorene 8, 2-methylfluorene 9, 1-methylfluorene 10, dibenzothiophene 11, phenanthrene 12, anthracene 13, methylphenanthrene/methylanthracene 14, methylphenan-threne/methylanthracene 15, 2-methylanthracene 16, 4,5-methylenephenanthrene 17, methylphenanthrene/methylanthracene 18,1-methylphenanthrene 19, fluoranthene 20, benzo(def)dibenzothiophene 21, pyrene 22, ethylmethylenephena-threne 23, benzo(a)fluorene 24, benzofb)fluorene 25, 4-methylpyrene 26, meth-ylpyrene 27, 1-methylpyrene 28, benzothionaphthene 29, benzo(c)phenanthrene 30, benzophenanthridine 31, benzo(2i)anthracene 32, chrysene/triphenylene 33, benzo(b)fluoranthene 34, benzof])fluoranthene 35, benzo(k)fluoranthene 36, ben-zo(c)pyrene 37, benzofa)pyrene 38, perylene 39, indenof 1,2,3-cd)pyrene 40, dibenz(a, /a,h)anthracenes 41, benzofghi)perylene 42, anthanthrene 43, coro-...

PSP = PhjPCHjCH SCHjCHjPPhj. b PC5P = PhjPCCH sPPhj. ° Ag is three-coordinate (P P) = 2,1 L-bis(diphenylphosphinomethyl)benzo[c]phenanthrene. d DPM - bis(diphenylphosphino)methane. 

Most of the diphosphine complexes of silver known are of the type AgXP2, where X is a halide and P2 is a diphosphine. In general, they adopt dimeric structures in the solid state, with the exception of the silver chloride complex of 2,ll-bis(diphenylphosphinomethyl)benzo[c]-phenanthrene which is monomeric. 

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