5,6-dimethyl-phenanthrene

Naphtho[2,l,8-(jira] naphthacene Naphtho[l,2-f>] triphenylene Ovalene Pentacene Pentaphene Perylene Phenanthrene Phenanthrene, dimethyl-Phenanthrene, methyl-Phenanthrene, tetramethyl-Picene Pyrene... 

The addition product, C QHgNa, called naphthalenesodium or sodium naphthalene complex, may be regarded as a resonance hybrid. The ether is more than just a solvent that promotes the reaction. StabiUty of the complex depends on the presence of the ether, and sodium can be Hberated by evaporating the ether or by dilution using an indifferent solvent, such as ethyl ether. A number of ether-type solvents are effective in complex preparation, such as methyl ethyl ether, ethylene glycol dimethyl ether, dioxane, and THF. Trimethyl amine also promotes complex formation. This reaction proceeds with all alkah metals. Other aromatic compounds, eg, diphenyl, anthracene, and phenanthrene, also form sodium complexes (16,20). 

B. HCl, m.p. 242-3°). The methiodide, m.p. 104-7°, of this, on treatment with potassium hydroxide in methyl aleohol, yielded 5 6-pimethoxy-8-vinylphenanthrene, m.p. 86-7°, along with dimethyl-de-iV-methylnorroemerine, oil, [aju + 13-55° (EtOH) the methiodide, m.p. 278°, of this, on like treatment also yielded 5 6-dimethoxy-8-vinyl-phenanthrene, whose identity was established by its oxidation by permanganate to 5 6-dimethoxyphenanthrene-8-earboxylie aeid. Rcemerine is, therefore, 5 6-methylenedioxy-iV-methylaporphine, and this eon-stitution has been confirmed by Marion and Grassie s synthesis of the alkaloid. 

Figure 6.10. Rate constants for quenching of sensitizers by cis- and trans-stilbenes (open and filled circles, respectively). Sensitizers are as follows (1) tri-phenylene, (2) thioxanthone, (3) phenanthrene, (4) 2-acetonaphthone, (3) 1-naphthyl phenyl ketone, (6) crysene, (7) fluorenone, (8) 1,2,5,6-dibenzanthracene, (9) benzil, (10) 1,2,3,4-dibenzanthracene, (11) pyrene, (12) 1,2-benzanthracene, (13) benzanthrone, (14) 3-acetyl pyrene, (15) acridine, (16) 9,10-dimethyl-l,2-benzanthracene, (17) anthracene, (18) 3,4-benzpyrene.<57> Reprinted by permission of the American Chemical Society.

The first carbocation in this series - (cw-1,2-dimethylvinyl)-9,l 0-dimethyl-phenanthrenium ion (la) was formed as a result of rearrangement of 1,2,2a, 10b-tetramethyl-2a,10b-dihydrocyclobuta[/]phenanthrene (2) in super-acids (Scheme... 

The 1H—NMR spectrum of 5,6,17,18-tetrahydro[2.2](2,7)phenan-threnopane (48) is compatible with the dihydrophenanthrene units being in an anti position. Dehydrogenation of 48 with 2,3-dichloro-5,6-dicyano-p-benzoquinone in benzene gave [2.2](2,7)phenanthrenophane which, owing to the similarity of its 1H—NMR spectrum to that of 2,7-dimethyl-phenanthrene, is assumed to have its phenanthrene units in the anti position 71>. 

These conclusions were not applicable when sediment was the source of hydrocarbons. McCain et al. (5) studied the bioavailability of petroleum in sediment to English sole (Parophrys vetu-lus). Sediments rich in alkylated and non-alkylated benzenes and naphthalenes, together with fluorene and phenanthrene, were employed. After 11 days of exposure, samples of skin, muscle, and liver were examined. Fluorene and phenanthrene were not accumulated in the test fish however, significant concentrations of 1-methyl naphthalene, 2-methyl naphthalene, 2,6-dimethyl naphthalene and 1,2,3,4-tetramethylbenzene, were found in skin and liver (Table II) 1-methyl naphthalene and 2-methyl naphthalene were the major components of muscle. In each tissue examined, 1-methyl-naphthalene was the major component 1,2,3,4-tetramethylbenzene occurred in relatively low concentrations in skin and muscle in comparison to naphthalenes containing one and two alkyl groups. 

For example, if one needs to know fC0W for 2,3-dimethyl-phenanthrene, and log P for phenanthrene is known to be 4.09 and nCH3 =0.71 for an aromatic ring substituent, the following relation could be used ... 

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

A parallel was drawn between stable ion and AMI studies of methylphenanthrenes and solvolytic studies of K-region and non-K-region phenanthrene oxides. The carbocation formed by opening of the 1,2-epoxide closely resembled the 2-methylphenanthrene cation (and 7H ), and the regiochemistry of phenol formation (1-phenanthrol) could be understood. Similarly, phenanthrenium cations derived from the 3-methyl and dimethylated compounds served as models for carbo-cations formed by solvolysis of phenanthrene-3,4-epoxide (formation of 4-phenanthrol following hydride shift). 

Sodium reacts with naphthalene in dimethyl ether to form a dark green reactive complex. This addition product, naphtalenesodium, CioHsNa, is stabilized by solvation with ether. Anthracene, phenanthrene, biphenyl, and many other aromatics form similar complexes with sodium in the presence of methylethyl ether, tetrahyrofuran, dioxane, and other ethers. 

Phenanthrene, fluoranthene, and pyrene—the three abundant parent PAHs identified by GC—were confirmed by MS. The major GC peaks between phenanthrene and fluoranthene were characterized as methyl- and dimethylphenanthrene/anthracene. Four compounds, each having a nominal mass of 192 amu were dejected. Small fragment ions at masses corresponding to (M-l), (M-27)+ and M", were detected. A general feature of these spectra was loss of a methyl group from the parent ion. The spectral features are characteristic of dimethyl or ethylphenanthrene/anthracene. 

GC-MS examination of the PAH fraction of sample S2 (S2-C2) gave very similar results the total ion chromatogram is shown in Figure 5. Major constituents were phenanthrene, fluoranthene, pyrene, and methyl, dimethyl/ethylphenanthrene/anthracene. Relative abundance of some C2-alkylphenanthrenes/anthracenes were higher in this sample than in S1-C2. Smaller quantities of benzo[ghi]fluoranthene, chrysene, benzo[ajanthracene, tripheny-lene, benzo[b,j, k]fluoranthenes, and benzo[e aJpyrenes and were characterized by MS. In addition, most compounds listed in Table 1 were also detected in this sample. 

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