Phenan threnes

The polycyclic aromatic hydrocarbons such as naphthalene, anthracene, and phenan-threne undergo electrophilic aromatic substitution and are generally more reactive than benzene. One reason is that the activation energy for formation of the c-complex is lower than for benzene because more of the initial resonance stabilization is retained in intermediates that have a fused benzene ring. 

Naphthalene, acenaphthane, acenaphthene, fluorene, phenan-threne, anthracene, fluoranthene, pyrene, benzanthracene, benzophenanthrene, and benzpyrene... 

Sodium-1,2,3,4a,4b,5,6,10,1 Qa Decahydro-1,4a-Dimethyl- 7-( 1 -Methylethyl) Phenan threne-1-Carboxylate (Sodium Abietate). 

The disadvantages of the Gomberg-Bachmann arylations are significantly reduced in their intramolecular analogues, particularly in Pschorr s synthesis of phenan-threne and related compounds. 

An important development has been the isolation of bacteria that were able to degrade phenan-threne that was sorbed to humic acid material (Vacca et al 2005). Enrichment was carried ont with PAH-contaminated soils using phenanthrene sorbed to commercial hnmic acid. Only the strains isolated from this enrichment were able to carry ont degradation of C-labeled phenanthrene, and this exceeded by factors of 4-9 the amonnt estimated to be available from the aqneons phase alone. It was snggested that specially adapted bacteria might interact specifically with natnrally occnrring colloidal material. 

Shiaris MP, JJ Cooney (1983) Replica plating method for estimating phenanthrene-utilizing and phenan-threne-cometabolizing microorganisms. Appl Environ Microbiol 45 706-710. 

Fig. 2.4f shows theuv spectra of azobenzene (Az, concentration 3,73 x 1Q 3 g dm- 3) and phenan-threne (P. 3.23 x 1G-3 g dm-3 both recorded in /.soocune. The wavelength dme on the instrument was 1U 11m cm" 1 and the absorbance range was 2 uufs. Measurements were made against wo-octane using 10 mm cells. 

Ren RXF, Chaudhuri NC, Paris PL, Rumney S IV, Kool ET (1996) Naphthalene, phenan-threne, and pyrene as DNA base analogues synthesis, structure, and fluorescence in DNA. J Am Chem Soc 118 7671-7678... 

Organic compounds polycyclic aromatic hydrocarbons, in particular phenan-threne (C14H10), pyrene (Ci6Hjo) and chrysene (CisH ), which were detected using high resolution mass spectrometry. 

Anthracene is hardened by about a factor of two by dissolving phenan-threne in it (Vaidya and Shah, 2003), but the authors do not state the solute concentration. 

Mesitonitrile oxide, but not benzonitrile oxide, adds to aza-analogs of phenan-threne, viz., benzo[/z]quinoline, 1,10-, 1,7-, and 4,7-phenanthrolines to give low yields of mono-cycloadducts at the C(5)=C(6> bond. Only 4,7-phenanthroline gave minor products, of which one the bisadduct 167 was isolated in approximately 7% yield. Phenanthridine reacts with two nitrile oxides but affords phenanthridin-6-one rather than a cyclo-adduct (336). 

An XRPD system equipped with a heatable sample holder has been described, which permitted highly defined heating up to 250°C [55]. The system was used to study the phase transformation of phenan-threne, and the dehydration of caffeine hydrate. An analysis scheme was developed for the data that permitted one to extract activation parameters for these solid-state reactions from a single non-isothermal study run at a constant heating rate. 

More easily than benzene, naphthalene can be oxidised directly to (a)-quinone this is the preparative method with anthracene and phenan-threne. 

Evaluating the effect of hydroxypropyl cyclodextrine (HPCD) on phenan-threne solubilization and biodegradation, showing HPCD significantly increased the apparent solubility (i.e., the bio availability) of phenanthrene, having a major impact on the biodegradation rate of phenanthrene [193]. 

Mixed coupling between naphthalene and alkyl benzenes has also been demonstrated (Table 10, numbers 10-13). The relative yield of mixed coupling products increases with the basicity of the alkyl benzene with mesitylene 19%, with tetramethylbenzene 42%, and with pen-tamethylbenzene 64%. This suggests an electrophilic reaction between naphthalene cation radicals and alkylbenzenes. The mixed coupling reaction of phenan-threne with anisole has been studied kinetically [163]. 

Aromatic hydrocarbon a hydrocarbon characterized by the presence of an aromatic ring or condensed aromatic rings benzene and substituted benzene, naphthalene and substituted naphthalene, phenan-threne and substituted phenan-threne, as well as the higher condensed ring systems compounds that are distinct from those of aliphatic compounds (q.v.) or ali-cyclic compounds (q.v.). 

The first cycloproparene prepared by this scheme was l//-cyclopropa[f>]phenan-threne (30), prepared by Billups et al. from diene 28 via adduct 29 as shown below. °... 

Steroids are compounds possessing the tetracyclic skeleton of cyclopenta[a]phenan-threne (1) or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Natural steroids have trivial names. The nomenclature of steroids is not based on these trivial names, but on a few stereoparent hydrides that are common to many compounds. Substitutive nomenclature is used to designate characteristic groups and unsaturation. Structural modifications are expressed by appropriate non-detachable prefixes. 

FIGURE 19.24 HPLC separation of a standard mixture of 16 EU-priority PAHs plus EPA-priority PAHs, benzo[e]pyrene and benzo[fc]chrysene. Na=naphthalene, Ac = acenaphthylene, E=fluorene, Pa=phenan-threne, A = anthracene, El = fluoranthene, P = pyrene, BcE = benzo[c]fluoranthene, CPP = cyclopenta[c,4] pyrene, BaA = benz[a]anthracene, Ch = chrysene, 5-MeCh = 5 methylchrysene, BeP = benzo[e]pyrene, BjE = benzo[/ ]fluoranthene, BbF = benzo[h]fluoranthene, BkE = benzo[l ]fluoranthene, BaP = benzo[a]pyrene, DBahA = dibenz[a,/j]anthracene, DBalP = dibenzo[a,l]pyrene, BghiP = benzo[g,/j,i]perylene, IP = indeno [l,2,3-c4]pyrene, DBaeP = dibenzo[a,e]pyrene, BbCh = benzo[h]chrisene, DBaiP = dibenzo[a,i]pyrene,... 

Perfluoro- 1,3- dimethyl- cyclohexane Perfluoro- n-octane Perfluor- decaline (cis+trans Isomere) Perfluoro- perhydro- phenan- threne... 

Rudolf Fittig, 1835-1910. Professor of organic chemistry at Tubingen and Strasbourg. He discovered the lactones, and devised a general method for synthesizing homologs of benzene. With Erdmann he established the constitution of phenan-threne, and with Remsen he proved the constitution of the alkaloid, piperme. Sir William Ramsay was one of his students. 

Finally, while several volatile and semivolatile PAHs, e.g., naphthalene, the methylnaphthalenes, phenan-threne, pyrene, and fluoranthene, are not significant mutagens or carcinogens (hence not included in Table 10.13), they are precursors to powerful direct bacterial mutagens formed in gas-phase atmospheric reactions with hydroxyl during the day and nitrate radicals at night (see Section F). Furthermore, 2-nitrofluoranthene,... 

In a laboratory environmental chamber study of the gas-phase photooxidation of naphthalene and phenan-threne, Sasaki and co-workers (1997b) found two products, 2-nitronaphthalene and 2-nitrodibenzopyranone (XI), that displayed significant genotoxicity in the MCL-5 human cell assay. This finding emphasized the importance of atmospheric reactions in forming mutagens, since the concentrations of such compounds are relatively high in ambient air compared to those expected for nitroarenes directly emitted from primary combustion sources (see Section F). 

In a similar study, Allen and co-workers (1996) determined the particle size distribution for 15 PAHs with molecular weights ranging from 178 (e.g., phenan-threne) to 300 (coronene) and associated with urban aerosols in Boston, Massachusetts. As for BaP in the winter (Venkataraman and Friedlander, 1994b), PAHs with MW >228 were primarily present in the fine aerosol fraction (Dp < 2 /Am). A study of 6-ring, MW 302 PAH at the same site showed bimodal distributions, with most of the mass in the 0.3- to 1.0-/zm particle size size range a smaller fraction was in the ultrafine mode particles (0.09-0.14 /xm) (Allen et al., 1998). For PAHs with MW 178—202, the compounds were approximately evenly distributed between the fine and coarse (D > 2 /am) fractions. Polycyclic aromatic hydrocarbons in size-segregated aerosols col-... 

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