Ethyl-9-phenanthrene

Ethyl-9-phenanthrene CH3-9-phenanthrenyl methyl 72.9 + 1.5 305.0 + 6.3 VLPP 1980MCM/TRE... 

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). 

Ethyl 1 /T-azepine-l-carboxylate (1) and l,3-diphenyl-2/7-cyclopenta[/]phenanthren-2-one (26) (phencyclone) in refluxing benzene undergo a rapid peri- and regioselective cycloaddition to give the [4 + 2] 7t-e rfn-adduct 28 and not, as was first proposed, a [6 + 2] 7r-adduct.264 Subsequently, however, it was found that at room temperature a [2 + 4] 7r-cw/<>-adduct 27 is formed which readily undergoes a Cope rearrangement to the [4 + 2] endo,anti-adduct 28. 

C17H21CIN2O4 59639-73-5) see Vincamine (135-cis)-13-ethyl-7,ll,12,13,16,17-hexahydro-3-methoxy-6//-cycIopenta[a]phenanthren-17-oI acetate ( 22112 03 2911-81-1) see Levonorgestrel 3-ethylhexahydro-3-(3-methoxyphenyl)-lH-azepine (C15H23NO 27180-90-1) see Meptazinol... 

The phenanthrene system appears to be no more easily cleaved than the naphthalene system however, ethyl anthracene is clearly destabilized significantly more than the other compounds in the table. The large decrease in bond-dissociation energy for the anthracene system is reflected in the increase by three to four orders of magnitude in the rate of scission at conversion temperatures, as shown in the table. 

The chemical sensitization effect was 0.006 (calculated from the quantum yield of the photochemical transformation of 130 to 131, the yield of 131 obtained with the oxalate/hydrogen peroxide reaction, and the moles of oxalate employed). Higher chemical sensitization efficiencies (about 0.04) were observed when the oxalate/hydrogen-peroxide system was used in the addition of ethyl vinyl ether onto phenanthrene quinone... 

I6 2,3-dimethylstyrene 38 (Crphenyl)ethyl tert-butyl ether (tentative) 63 phenanthrene... 

Drake, N. L., and T. R. Sweeney The Reaction of Phenanthrene with Ethyl... 

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. 3,8-Dimethoxy-4,5,6,7-dibenzo-l,2-dioxacyclooctane. Theozo-nolysis of 10 g. (0.0562 mole) of phenanthrene in dry methanol is carried out as described in the diphenaldehyde preparation (p. 41). The reaction mixture is not reduced, however, but is acidified with 1-3 drops of concentrated hydrochloric acid (Note 1) and allowed to stand at room temperature for an hour and then in the refrigerator for several hours or overnight. Suction filtration yields 11.5-12.5 g. (75-82%) of crystals melting at 178-181°. Trituration with methyl ethyl ketone gives a 90-95% recovery of colorless crystals melting at 180-181° (Note 2). 

Thermochemical data are available (Ref 2) on the heats of combustion and formation for all five isomers, on the heats of nitration from various Dinitrotoluenes for the 23,4-, 2,4,5-, and 2,3,6-isomers, and on the heats of crystn for the 2,3,4- and 2,4,5-isomers. Data are also available (Ref 1) on the shock sensitivities of all of the isomers except 2,3,6-, and on the rates of decompn at 140° of the 23,4-, 2,4,5-, and 23,5-isomers. The detonation pressure and the temp coefficient of decompn between 140 and 180° have been measured for the 2,4,5-isomer 2,3,4- and 2,4,5-TNT form addition compds ( 7r-complexes ) at 1 1 molar ratio with several polycyclic aromatic hydrocarbons (naphthalene, acenaphthene, fluorene, phenanthrene and anthracene) (Ref 2). 2,4,5-TNT forms complexes with 4-aminozaobenzene, 4-aminoacetophenone, bis (2 hydroxy ethyl) amine, and tris (2-hydroxy-ethyl) amine (Ref 1). The first two have a 1 1 molar ratio, the third 1 2, and the fourth 2 1. Upon heating, the two 4-amino compds react with replacement of the 5-nitro group, as discussed below... 

Phenanthrene and pyrene on treatment with diisopropylcarbodiimide, hydrogen peroxide, and acetic acid in ethyl acetate at room temperature give 1 and 4 in 28% and 27% yields, respectively.17 Similar reaction occurs with dicyclohexylcarbodiimide and cyclohexylbenzylcarbodiimide. The hydrogen peroxide can be either 98% or a 30% aqueous solution. Use of silica gel, Dowex 50W-X8, or diphenylphosphinic acid instead of acetic acid is also permissible. However, because of the sensitivity of arene oxides toward strong acids, hydrochloric, sulfuric, or polyphosphoric acids cannot be used. 

Analogous results are also obtained with the hydrogenated forms of ace-napthene (7),fluorene (8) and phenanthrene (9) as shown in Eq. (4-6) 13 15>. In each case (Scheme 1 and Eq. (4—6)) significant amounts of non bridgehead alkyladamantanes were obtained as the first formed adamantanes 14> 15 Further rearrangement led to the build-up of the indicated intermediates. In all cases, the first all bridgehead adamantane intermediate contained a 1-ethyl group 14> ls). 

PHENANTHRENE-2-ACRYLIC ACID. 4b 5.6.7>8,8a,9 10-OCTAHYORO-8-CARBOXY-3-HETHOXY-beta.4b.8-TRIMETHYL-. 2-ETHYL ESTER. 8-METHYL ESTER... 

Polyaromatic hydrocarbons and parabenes (ethyl-hexyl parabene, naphthalene, fluo-rene, phenanthrene, fluoranthene, pentylbenzene) Excil C18 Acetonitrile-Tris HC1 buffer pH 8.0 (80 20) 380 mm x 100 pm i.d. 85 mm packed length... 

Polyaromatic hydrocarbons and parabenes (thiourea, ethyl-hexylparabene, naphthalene, fluorene, phenanthrene, anthracene, fluoranthene)... 

Oxidative cyclization, substituted stil-benes to phenanthrenes, 46, 91 2-Oxocyclooctanecarboxylic acid, ETHYL ESTER, 47, 20 4-Oxo-l, 1-dimethylpiperidinium salts, 45,82... 

Preparation of 8-oxo-8H-5-oxa-l-aza-phenanthrene-6-carboxylic acid ethyl ester... 

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