Phenanthrene hydro

The synthetic procedure described is based on that reported earlier for the synthesis on a smaller scale of anthracene, benz[a]anthracene, chrysene, dibenz[a,c]anthracene, and phenanthrene in excellent yields from the corresponding quinones. Although reduction of quinones with HI and phosphorus was described in the older literature, relatively drastic conditions were employed and mixtures of polyhydrogenated derivatives were the principal products. The relatively milder experimental procedure employed herein appears generally applicable to the reduction of both ortho- and para-quinones directly to the fully aromatic polycyclic arenes. The method is apparently inapplicable to quinones having an olefinic bond, such as o-naphthoquinone, since an analogous reaction of the latter provides a product of undetermined structure (unpublished result). As shown previously, phenols and hydro-quinones, implicated as intermediates in the reduction of quinones by HI, can also be smoothly deoxygenated to fully aromatic polycyclic arenes under conditions similar to those described herein. 

Diacyl-biphenyle4 gehcn bei der Reduktion in 9,10-Dihydroxy-9,10-di-hydro-phenanthrene (70—90% d. Th, c/s/tram-Gcmische) iiber3 4 ... 

Reduction of stilbene [18] or dipheny-lacetylene [214] in DME yields 1,2,3,4-tetraphenylbutane, whereas phenanthrene [214] provides 9,9, 10,10 -tetra-hydro-9.9 -biphenanthrene. Hydrodimerization was also observed with benzalfluo-rene [225]. If DME is replaced by acetonitrile, protonation completely dominates hydrodimerization [18]. In carefully dried ethers, using alkali or alkaline earth metals salts as supporting electrolyte, 1,1-diphenylethylene can be reduced ca-thodicaUy to give stable solutions of 1,1,4,4-tetraphenylbutane dianions [226]. These dianions can be cleaved by flash... 

A combined effect of natural organic matter and surfactants on the apparent solubility of polycyclic aromatic hydrocarbons (PAHs) is reported in the paper of Cho et al. (2002). Kinetic studies were conducted to compare solubilization of hydro-phobic contaminants such as naphthalene, phenanthrene, and pyrene into distilled water and aqueous solutions containing natural organic matter (NOM) and sodium dodecyl sulfate (SDS) surfactant. The results obtained after 72hr equilibration are reproduced in Fig. 8.19. The apparent solubility of the three contaminants was higher in SDS and NOM solutions than the solubility of these compounds in distilled water. When a combined SDS-NOM aqueous solution was used, the apparent solubility of naphthalene, phenanthrene, and pyrene was lower than in the NOM-aqueous solution. 

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 relative performances of the two autoclaves were compared by the use of ratios. Three ratios were derived utilising (a) the unconverted phenanthrene, denoted by P (b) the amounts of the various hydro-derivatives of phenanthrene multiplied by the relative number of hydrogens added, eg % tetrahydrophenanthrene 4, denoted by HP (c) the total content of hydrocracked compounds, denoted by C. These ratios would indicate the reactivity of the autoclaves and their relative abilities towards hydrogenation and hydrocracking. 

Sensitized P-Type Delayed Fluorescence phenanthrene/anthracene, anthracene/naphthacene, phenanthrene/naphthalene, proflavine hydro-chloride/anthracene. Undoubtedly, many more examples will soon be found. 

For the preparation of chlorides or bromides, the diazonium salt is decomposed with a solution of cuprous chloride or bromide in the corresponding halogen acid (Sandmeyer reaction). It is possible to prepare the aryl bromide from the diazonium chloride or sulfate. A variation Involves the use of copper powder and a mineral acid for the decomposition step (Gattermann reaction). Both procedures are illustrated by the syntheses of the isomeric bromotoluenes and chlorotoluenes. The usual conditions of the Sandmeyer reaction fail in the preparation of the chloro- and bromo-phenanthrenes. However, these compounds can be successfully obtained by the interaction of the diazonium compound with mercuric and potassium halides (Schwechten procedure). Another procedure for formation of aryl bromides involves treatment of the amine hydrobromide with nitrogen trioxide in the presence of excess 40% hydro-bromic acid. The Intermediate diazonium perbromide is then decomposed by heat. ... 

Fluorene has been reported to afford the 3,9a-dihydro product, but it is almost certain that this is the 2,4a-dihydro isomer (55 = 1) by analogy with biphenyl. 9,10-Dihydrophenanthrene (56) is reduced as expected to (55 n = 2), but spontaneously reverts to the starting material on standing. These systems do not require the presence of alcohol for reduction and it is consequently possible to alkylate the intermediate anions with alkyl halides, as (56) gives (57). These products are much more stable and structural analysis is simplified accordingly oxidation of the doubly allylic methylene occurs readily to afford the dienone (58 Scheme 7). Dienones of this type have potential as intermediates for the synthesis of natural products. Anthracene and phenanthrene are both readily reduced in the central ring to form the 9,10-di-hydro derivatives as might be expected, but to avoid further reduction it is necessary to have an iron salt present. Further examples are reviewed elsewhere. ... 

A similar removal of benzeneselenenic acid from l,l-dichloro-la-phenylseleninyl-la,9b-di-hydro-l//-cyclopropa[/]phenanthrene (2) at ambient temperature was used to generate 1,1-dichloro-l//-cyclopropa[/]phenanthrene as a short-lived intermediate which was trapped by addition of methanol.Elimination of the elements of HSe Mcj from 3, derived from la-methylselenacyclopropa[/]phenanthrene and la,9b-dihydro-l//-cyclopropa[/]phenanthrene after alkylation, gave a mixture of the alternative cyclopropene, which were both trapped with furan. 

R-(1 a,4ap,4ba,10aa)]-1,2,3,4,4a,4b,5,6,10,1 Oa-Deca-hydro-1,4a-dimethyi-7-(1-methylethyl)-1-phenanthrene-carboxyllcacid, 7,13-Abietadien-18-olc acid Abietate Abietic acid l-Abietic acid AI3-17273 CCRIS 3183 EINECS 208-178-3 13-... 

It should be noted that NBS can cause nuclear bromination when that reaction occurs readily. In the absence of a catalyst it can brominate the nucleus of condensed aromatic compounds such as naphthalene, anthracene, and phenanthrene,399 veratrole, the dimethyl ethers of resorcinol and hydro-quinone,389 and pyrogallol trimethyl ether.390 Pyrocatechol and 2 moles of NBS afford 4,5-dibromopyrocatechol resorcinol and 3 moles of NBS afford 2,4,6-tribromoresorcinol 391,392 and anthranilic or o- or/ -hydroxybenzoic acid with 2 moles of NBS afford the 4,5- or 3,5-dibromo derivatives.391-393 However, nuclear bromination of benzene and toluene is effected by NBS only if equimolar amounts of A1C13, ZnCl2, FeCl3, or H2S04 are added. 

Diketones from hydroxy-a,j -ethyleneketones via diols—Robinson hydro-phenanthrene ring synthesis s. 16, 871... 

Because PAHs exhibit a range in lipophilic affinity, elimination that relies solely on passive diffusion loss should be slower for the more hydro-phobic PAHs. Such a correlation has been shown for the freshwater amphi-pod [Diporeia spp. (Pontoporeia hoyi)], which does not metabolize PAHs to any appreciable extent (Landrum 1988). This author found that for a series of PAHs with increasing octanol-water partition coefficients, the elimination constant decreased, which led to longer half-lives. The more water-soluble PAHs phenanthrene, anthracene, and fluoranthene showed nearly identical rapid elimination patterns (/./, 2 d) in mussels (Mytilus edulis) exposed to contaminated suspended sediments for 28 d, while the more hydrophobic PAHs produced half-lives in the range of 4-6 d (Fig. 8 see Table 2) (Lake et al. 1985). The most hydrophobic of the group, pery-lene, displayed the slowest elimination. 

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