Phenanthrene and derivs

Phenanthrene and Derivatives. Activity in the field of phenanthrene synthesis has been considerable. Photodehydrocyclization of stilbenes has been mentioned earlier, and a similar reaction of 2-methoxy-4,5-dimethylstilbene (363) leads to l-methoxy-3,4-dimethylphenanthrene (364) and 2,3-dimethylphenanthrene... 

This cyclization also gives good results in the case of derivatives of naphthalene, anthracene, phenanthrene, and other aromatic substrates [76]... 

Rather similar was the paper [PolG36a] which also derives asymptotic formulae for the number of several kinds of chemical compounds, for example the alcohols and benzene and naphthalene derivatives. Unlike the paper previously mentioned, this one gives proofs of the recursion formulae from which the asymptotic results are derived. A third paper on this topic [PolG36] covers the same sort of ground but ranges more broadly over the chemical compounds. Derivatives of anthracene, pyrene, phenanthrene, and thiophene are considered as well as primary, secondary, and tertiary alcohols, esters, and ketones. In this paper Polya addresses the question of enumerating stereoisomers -- a topic to which we shall return later. 

Photoredox systems involving carbonyl compounds and amines are used in many applications. Carbonyl compounds employed include benzophenone and derivatives, a-diketones [e.g. benzil, cainphoroquinone (85),2W 291 9,10-phenanthrene quinone], and xanthone and coumarin derivatives. The amines are tertiary and must have a-hydrogens [e.g. N,A7-dimethylani 1 ine, Michler s ketone (86)]. The radicals formed are an a-aminoalkyl radical and a ketyl radical. 

Numerous molecular compds of phenanthrene and its derivatives have been reported with perchloric acid, PA, styphnic acid, sym-TNT, sym-TNB, and Tetryl. These compds are useful for identification purposes because many have sharp melting points but none have been reported to be expl... 

The plant is known elaborate a series of quite unusual phenanthrene alkaloid derivatives, of which aristoliukine-C, aristofolin A and E, aristolochic acid-la methyl ester, and aristolochic acid. Other chemical constituents found in this plant are flavonoid glycosides such as kaempferol-3-O-rutinoside and quercetin kaempferol-3-O-rutinoside (3,4). Exposure to Aristolochiaceae family is associated with the development of cancer in humans. A significant advance is the toxicological effects of aristolochic acid has been provided by the work of Pezzuto et al. They showed that aristolochic acid is a mutagen... 

Human activities have resulted in exposure of Antarctic fishes to petroleum-derived PAHs (McDonald et al. 1992). Fish captured near Palmer station on the Antarctic peninsula had induced EROD activities and elevated concentrations of biliary PAH metabolites of phenanthrene and naphthalene when compared to conspecifics from reference sites (McDonald et al. 1995). Artificial reefs consisting of oil and coal flyash stabilized with cement and lime in Florida waters near Vero Beach contained elevated PAH levels ranging from as high as 1.2 mg fluoranthene/kg and 0.25 mg naphthalene/kg. But there is negligible leaching because seawater is not an effective medium for removing PAHs from reef bricks or the ash (Frease and Windsor 1991). 

Aromatic molecules with no polar substituent include benzene derivatives or other, more polyaromatic molecules, such as naphthalene, phenanthrene, and anthracene. These are polarizable. Paraffins are not polarizable by comparison. In gas-liquid systems, aromatic molecules will show stronger interactions with polar stationary phases that paraffins of comparable boiling point and, thus, polar stationary phases can aid in improving separation of substituted aromatics. 

Emulsions based on lipophilic iodized and/or bromated substances with emulsifiers and derivatives of cyclopenta-phenanthrene Polyiodinated phenyl fatty acid compoimds Emulsion of iodinated lipids 6-Iodoethylated starch... 

All the hydrocracking/hydrogenation experiments were carried out in 500 ml capacity spinning type autoclaves. Two autoclaves of this design were used and the autoclaves were compared in experiments using the model compound phenanthrene, chosen because phenanthrene and its hydro-derivatives represent a large proportion of the solvent which is recycled in coal liquefaction processes. 

The mixture of agonists-antagonists includes derivatives of morphinane (nalorphine, butorphanol), phenanthrene (nalbuphine), derivatives of benzomorphane (pentazocine, dezocine), and derivatives of opipravin (buprenorphine). 

Two or more benzene rings fused together form a number of polycyclic benzenoid aromatic compounds, naphthalene, anthracene and phenanthrene, and their derivatives. All these hydrocarbons are obtained from coal tar. Naphthalene is the most abundant (5%) of all constituents of coal tar. 

Opium alkaloids and derived phenanthrene alkaloids codeine, morphine, (Avinza, Kadian, MSContin, Roxanol), hydromorphone (Dilaudid), oxymorphone (Numorphan), oxycodone (dihydroxycodeinone, a component of Oxycotin, Oxydose, Oxyfast, Percodan, Percocet, Roxicodone, Tylox)... 

The infrared (IR) spectra of 1,10-phenanthroline, its hydrate and perchlorate in the region 600-2000 cm-1 have been obtained, and the principal features of the spectra interpreted.66 Further studies on the IR spectra of 1,10-phenanthroline,67-69 substituted 1,10-phenanthrolines,70,71 and 1,7-phenanthroline67 have also been reported. The IR spectrum of 4,7-phenanthroline in the region 650-900 cm-1 has been analyzed, and the C—H out-of-plane deformation frequencies were compared with those of phenanthrene and benzo[/]quinoline.72 The IR spectra of salts of 1,10-phenanthroline have been taken, and the NH vibrations determined.28,73 Infrared spectroscopy has been used to detect water associated with 1,10-phenanthroline and some of its derivatives on extraction into nitromethane from aqueous solution.74 The Raman spectrum of 1,10-phenanthroline has been compared with its IR spectrum.75 Recently, the Raman and IR spectra of all ten isomeric phenanthrolines were measured in solution and solid states, and the spectra were fully discussed.76... 

The photocyclization of stilbene and its simple derivatives to phenanthrene and substituted phenanthrenes is now a well-documented and useful synthetic reaction the scope and mechanism of this reaction have been thoroughly reviewed by Stermitz.344 There... 

The first arene oxides to be synthesized (1964) were obtained by the cyclization of appropriate seco derivatives. 0,0-Diformylbiphenyl derivatives, when treated with Mark s reagent [tris(dimethylamino)phosphine], gave arene oxides [Eq. (3)]. Thus K-region epoxides from phenanthrene and its analogs, benz[a]anthracene and its 7,12-dimethyl analog, have been prepared.34... 

Reactions of K-region arene oxides derived from phenanthrene and 7,12-dimethylbenz[a] anthracene with nucleosides have been studied with a view to assessing the carcinogenicity of the products obtained.199... 

For phenanthrene hydrate the derived value of p fR is —11.6. This is comparable to values for the benzhydryl (-12.5) or / -methylphenethyl (-12.8) cations.22,69,73 The evaluation of p fR as well as pKa allows derivation of p h2o = pA"R — pKa = 9.3. This equilibrium constant offers a measure of the stability of the 9,10-double bond of phenanthrene and thus the aromaticity of its central benzene ring. Comparison with the double bond of 2-butene, for which p h2o = —3.94,86 indicates a 1013-fold greater stability, for the aromatic double bond. It should be noted that the value of p h2o does not depend on azide trapping. In the difference between p fR and pKA the rate constant kAz cancels out and K o = kAkn2o/knkp. 

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