Of phenanthrenes

Diphenic acid. Phenanthrene upon oxidation in acetic acid solution at 85° with 30 per cent, hydrogen peroxide gives diphenic acid (diphenyl-2 2 -di-carboxyHc acid) no phenanthraquinone is formed under these experimental conditions. The reaction is essentially an oxidation of phenanthrene with peracetic acid. (For another method of preparation, see Section I V,74.)... 

The best example of the class of phenanthrene-methanols is halofantrine (66, Halfan [36167-63-2]) a dmg that is effective against chloroquine-resistant malaria and is now being evaluated in Africa. It produces temporary gastrointestinal disturbances. 

Reduction of phenanthrene-9,10-dione with HI in acetic acid afforded 9-hydroxyphenanthrene as sole product, while an analogous reaction without acetic acid furnished phenanthrene essentially quantitatively. 

Consider the two structures shown for kekulene, one suggesting inner and outer annulenes, and the other a series of phenanthrene-like units. Indicate properties that you would expect to be associated with each structure. Proton NMR and bond-length data are given. How do they compare with your expectations ... 

For the synthesis of phenanthrene derivatives whieh may be regarded as an approaeh to eolehieine as formulated by Windaus, see Windaus and Eiehel, Sharp, and Grewe. ... 

There are five resonance structures of phenanthrene, one of winch is shown. Draw the other four. 

Robin57 59 studied this system up to 1000 atm. He measured the concentration of phenanthrene from its light absorption—a method that can only be used where a careful study has been made of the direct effect of pressure on the spectrum. He studied the direct effect in separate experiments with unsaturated solutions. 

Phenanthrene Diozonide.C14H102O3. Harries and Weiss in 1905 reported that the ozonolysis of phenanthrene in chlf soln produced a crystn, expl diozonide (Refs 2 4). Subsequently, very detailed studies of the ozonolysis reaction of phenanthrene by three different groups of investigators failed to confirm the existence... 

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 classical syntheses of phenanthrene and fluorenone fit well into the electron transfer scheme discussed in Section 8.6 and in this chapter. The aryl radical is formed by electron transfer from a Cu1 ion, iodide ion, pyridine, hypophosphorous acid, or by electrochemical transfer. The aryl radical attacks the neighboring phenyl ring, and the oxidized electron transfer reagent (e. g., Cu11) reduces the hexadienyl radical to the arenium ion, which is finally deprotonated by the solvent (Scheme 10-76). 

Intramolecular arylations can also be carried out photochemically. Huisgen and Zahler (1963 a) prepared fluoren-9-one by irradiation of benzophenone-diazonium salts in dilute sulfuric acid. The classical Pschorr synthesis of phenanthrene-9-carb-... 

Selective adsorption of phenanthrene on activated carbons for surfactant reuse in soil washing process... 

Effectiveness of selective adsorption of phenanthrene in Triton X-100 solution depends on surface area, pore size distribution, and surface chemical properties of adsorbents. Since the micellar structure is not rigid, the monomer enters the pores and is adsorbed on the internal surfaces. The size of a monomer of Triton X-100 (27 A) is larger than phenanthrene (11.8 A) [4]. Therefore, only phenanthrene enters micropores with width between 11.8 A and 27 A. Table 1 shows that the area only for phenanthrene adsorption is the highest for 20 40 mesh. From XPS results, the carbon content on the surfaces was increased with decreasing particle size. Thus, 20 40 mesh activated carbon is more beneficial for selective adsorption of phenanthrene compared to Triton X-100. 

Fig. 2. Adsorption isotherm of phenanthrene on the activated carbons. Table 2...

Phenanthrene dissolved in Triton X-100 solution was separated by sorption with three GACs with different particle size (4 12,12 20, and 20 40 mesh). The highest adsorption selectivity was obtained with the 20 40 mesh over a wide concentration range of phenanthrene and Triton X-100. The results demonstrate that the selective adsorption is potentially effective to reuse surfactants in a soil-washing process for the remediation of contaminated soils. 

The photochemical transformation of phenanthrene sorbed on silica gel (Barbas et al. 1996) resulted in a variety of products including c -9,10-dihydrodihydroxyphenanthrene, phenanthrene-9,10-quinone, and a number of ring fission products including biphenyl-2,2 -dicarboxaldehyde, naphthalene-l,2-dicarboxylic acid, and benzo[c]coumarin. 

FIGURE 1.18 Product from the photochemical reaction of phenanthrene and NO. ... 

Barbas JT, ME Sigman, R Dabestani (1996) Photochemical oxidation of phenanthrene sorbed on silica gel. Environ Sci Technol 30 1776-1780. 

Boldrin B, A Tiehm, C Fritzsche (1993) Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Appl Environ Microbiol 59 1927-1930. 

Guerin WF, GE Jones (1988) Mineralization of phenanthrene by sl Mycobacterium sp. Appl Environ Microbiol 54 937-944. 

Kiyohara H, K Nagao, R Nomi (1976) Degradation of phenanthrene through o-phthalate by an Aeromonas sp. Agric Biol Chem 40 1075-1082. 

Narro ML, CE Cerniglia, C Van Baalen, DT Gibson (1992) Metabolism of phenanthrene by the marine cyanobacterium Agmc c// m quadruplicatum PR-6. Appl Environ Microbiol 58 1351-1359. 

Sutherland JB, AL Selby, JP Freeman, FE Evans, CE Cerniglia (1991) Metabolism of phenanthrene by Phanerochaete chrysosporium. Appl Environ Microbiol 57 3310-3316. 

The transformation of benzene, toluene, naphthalene, biphenyl, and benzo[a]pyrene to the corresponding phenols (Trower et al. 1989) by Streptomyces griseus, and of phenanthrene by Streptomyces flavovirens to ( )tran5 -[95, 105 ]-9,10-dihydrodihydroxyphenanthrene with minor amounts of 9-hydroxyphenanthrene (Sutherland et al. 1990). 

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