Anthracene-9-methanol

Aroyl esters of anthracene-9-methanol are photolysed in methanol to give products consistent with the anthracene-9-methyl cation as an intermediate.41 Rate constants for the solvolyses of secondary alkyl tosylates in fluorinated solvents were analysed in terms of the possible involvement of very short-lived carbocation-tosylate ion pair intermediates.42 The effect of added electrolytes on the rate of solvolysis of cumyl chloride and its -methyl derivative was studied in 90% aqueous acetone and 80% aqueous DMSO, with the results revealing a combination of a special salt effect and a mass law effect.43 Kinetic parameters obtained for the solvolysis of (8) (R1 = R2 = Me and R1 = Ar, R2 = H) show that there is substantial n, n participation in the transition state [e.g. (9). 44... 

Exp. 49, "Diels-Alder Reaction with Anthracene-9-methanol"... 

In a 50-mL round-bottom flask equipped with a stir bar, add 0.066 g of anthracene-9-methanol. Using a 25-mL graduated cylinder, add 25 mL of de-ionized water. Note that anthracene-9-methanol is insoluble in water. Add 0.070 g of N-methylmaleimide to the mixture, and fit the flask to a water-cooled condenser. Heat the mixture until it is boiling under reflux, and allow the reaction to continue boiling for 90 minutes while stirring. 

EXPERIMENT 48 The Diels-Alder Reaction with Anthracene-9-methanol... 

The Diels-Alder reaction with anthracene-9-methanol from Experiment 48. This compound possesses diastereotopic methylene protons, H, and H. ... 

N,N-Diethyl-m-toluamide (OEF), new procedure Diels-Alder Reaction with Anthracene-9-methanol Identification of Unknowns, revised procedure Competing Nucleophiles in S l and Sj. 2 Reactions Investigations Using 2-Pentanol and 3-Pentanol Friedel-Crafts, more substrates added Aqueous-Based Organozinc Reactions... 

B. Diastereotopic Hydrogens The Diels-Alder Adduct of Anthracene-9-methanol and N-Methylmaleimide... 

FIGURE 7.24 The 500 MHz NMR spectrum (CDCI3) of the Diels-Alder product of anthracene-9-methanol and A -methylmaleimide. The insets show expansions of the regions from 3.25 to 3.40 ppm and 4.7 to 5.2 ppm. The eight aromatic ring protons are not shown. Pavia, D. L., G. M. Lampman, G. S. Kiiz, R. 

A reactor flask was charged with methacrylate ester of 9-anthracene methanol (4.2 g), 4-acetoxystyrene (13.8 g), 2,2 -azobisisobutylonitrile (0.8 g), and propyleneglycol monomethylether and then vented for 15 minutes. The reaction mixture was then heated to 70°C for 5 hours and then cooled to ambient temperature and treated with 26 wt% aqueous tetramethylammonium hydroxide (7 g). The reaction temperature was then raised to 40°C for 3 hours and then further raised to 60°C for 8 hours. The mixture was then recooled to ambient temperature and acidified to a pH of 6 using acetic acid. The polymer was precipitated in 600 ml of methanol and the solid filtered, washed with methanol and deionized water, and dried. The precipitated polymer was redissolved in propyleneglycol monomethylether (60 g) and reprecipitated in 600 ml methanol. The solid was refiltered, rewashed, dried at 40°C, and the product isolated having an Mw of 12,800 Da with an Mn of 5400 Da. 

Figure 8.12 Chromatography of anthracene derivatives with different detection modes (A) laser-induced fluorescence (B) UV absorbance. Conditions capillary, 115.1 cm X 10 /un I.D. with 1.27-/im coating stationary phase, silicone acrylate/ethylhexyl acrylate Vy Vm = 0.65 mobile phase, acetonitrile detection, (A) laser-induced fluorescence (AeX 325 nm, Aem 380 nm), pressure 13.8 bar, (B) UV (258 nm), pressure 13.0 bar. Peaks 1, salicylate 2, anthracene-methanol 3, anthracenecarbonitrile 4, anthracene 5, fluoranthracene 6,1,2-benzanthracene 7, 9-phenylanthracene. (Reprinted from Ref. 11 with permission.)...

When sublimed, anthraquinone forms a pale yeUow, crystalline material, needle-like in shape. Unlike anthracene, it exhibits no fluorescence. It melts at 286°C and boils at 379°—381°C. At much higher temperatures, decomposition occurs. Anthraquinone has only a slight solubiUty in alcohol or benzene and is best recrystallized from glacial acetic acid or high boiling solvents such as nitrobenzene or dichlorobenzene. It is very soluble in concentrated sulfuric acid. In methanol, uv absorptions of anthraquinone are at 250 nm (e = 4.98), 270 nm (4.5), and 325 nm (4.02) (4). In the it spectmm, the double aUyflc ketone absorbs at 5.95 p.m (1681 cm ), and the aromatic double bond absorbs at 6.25 p.m (1600 cm ) and 6.30 pm (1587 cm ). 

Polyethylene glycol 4000 primary, secondary, tertiary alcohols as anthracene-urethane denvatives stabilization and enhancement saturated dipping solution in methanol [275]... 

Anthracene, dimethyl fumarate, and aluminum chloride give the adduct in 2 hours. When 2 molar equivalents of aluminum chloride are used, the reaction is complete in 5 minutes. The product is recrystallized from methanol, mp 108-109°. 

A solution of 10 g of 9 10-dihydro-9 10-ethano-(1 2)-anthracene-(9)aldehyde (made from anthracene and acrolein) and 10 g of monomethylamine in 100 cc of ethanol is heated at 80°C for 4 hours in an autoclave. The reaction mixture is then evaporated to dryness under reduced pressure to leave a crystalline residue which is dissolved in 150 cc of ethanol and, after the addition of 2 g of Raney nickel, hydrogenated at 40°C under atmospheric pressure. When the absorption of hydrogen has subsided, the catalyst is filtered off and the filtrate evaporated under reduced pressure. An oil remains which is covered with 100 cc of 2N hydrochloric acid. The 9-methylamino-methyI-9 10-dihydro-9 10-ethano-(9 10)-anthracene hydrochloride crystallizes immediately after crystallization from methanol it melts at 320°-322°C. 

The column used was a Pecosphere 3 mm in diameter and 3 cm long carrying a Cl8 stationary phase. The mobile phase was a mixture of methanol (75%) and water (25%) at a flow rate of 2 ml/min. The solutes were 1 benzene, 2 toluene, 3 ethyl benzene, 4 isopropyl benzene, 5 t-butylbenzene, 6 anthracene, and 7 sodium chloride. 

In most cases, the linear absorption is measured with standard spectrometers, and the fluorescence properties are obtained with commercially available spectrofluo-rometers using reference samples with well-known <1>F for calibration of the fluorescence quantum yield. In the ultraviolet and visible range, there are many well-known fluorescence quantum yield standards. Anthracene in ethanol (Cresyl Violet in methanol (commonly used reference samples for wavelengths of 350-650 nm. For wavelengths longer than 650 nm, there is a lack of fluorescence references. Recently, a photochemically stable, D-ji-D polymethine molecule has been proposed as a fluorescence standard near 800 nm [57]. This molecule, PD 2631 (chemical structure shown in Fig. 5) in ethanol, has linear absorption and fluorescence spectra of the reference PD 2631 in ethanol to... 

Figure 4. Stern-Volmer plots and quenching constants derived from the fluorescence quenching of DMA (T), 1,2,3,4-tetra-hydro-BA ( ), 5,6-dihydro-BA (A), 8,9,10,11-tetrahydro-BA ( ) and anthracene ( ) by DNA in 15% methanol at 23° C. Emission and excitation wavelengths and details concerning the experimental conditions are given in refs. 12 and 14. The open symbols, o and V, show I /I for 1,2,3,4-tetrahydro-BA and DMA respectively in denatured DNA([P04"] 4.4 x 10 4 M).

The ladder polysilanes also show interesting photochemistry on irradiation with a high-pressure mercury lamp, the tricyclic ladder extruded the transient intermediate four-membered cyclic disilene which could be trapped using methanol, 1,3-butadiene, and anthracene, as shown in Scheme 38. 

Frequently it is convenient, when conducting sorption experiments, to use a cosolvent such as methanol to facilitate transfer of a volatile or insoluble solute. Equation 31 may be used to estimate the effect of the cosolvent on measured sorption coefficient. If fc equals 10- and a is conservatively chosen as unity, the methanol is predicted to decrease the sorption of anthracene (ac = 9.76 log Kow = 4.54 50) by 1% relative to the case of no cosolvent. The effect of the cosolvent should be smaller for solutes with smaller HSA (or KQW), which is consistent with the observed negligible impact of methanol at f. < 10 3.6 52). ... 

Fig. 16. CEC separation of naphthalene (1), fluorene (2), phenanthrene (3), anthracene (4), pyrene (5),triphenylene (6),andbenzo(a)pyrene (7) using capillary filled with CIO alkyl substituted polyallylamine. (Reprinted with permission from [86]. Copyright 1997 Elsevier). Conditions capillary 50 pm i.d., 48 cm total length, 33 cm active length, field strength 400 V/cm, carrier concentration 20 mg/ml, mobile phase 60 40 methanol-20 mmol/1 borate buffer pH=9.3...

The bisanthraceno-crown ether E-l (Figure 10.26) exhibits a fluorescence spectrum composed of the characteristic monomer and excimer bands. Gradual addition of sodium perchlorate to a solution in methanol induces a decrease in the monomer band and an increase in the excimer band. Complexation is indeed expected to bring closer together the two anthracene units, which favors excimer formation. A 2 1 (metabligand) complex is formed with Na+ in methanol and acetonitrile with a positive cooperative effect (see Appendix B). Interestingly, the overall stability constant obtained from absorption data was found to be lower than that... 

The observed fluorescence, UV, and H NMR perturbations of the Cd(II)-5d complex are observed only in water in methanol, ethanol, and acetonitrile only unperturbed anthracenic spectra are observed. 

The treatment of the bromoacetal (255) with catalytic amounts ( 10%) of a Co(I) species, generated by the electroreduction of cobaloxime (232) in an Me0H-LiCl04 system at —1.8 V, produces the cis-fused adduct (256) in 60 70% yield (Scheme 96) [392]. Cathodic reduction is used for the synthesis of a [Co(CO)3PBu3] complex in a methanol-methyl formate medium, which catalyzes the alkoxycarbonylation of dichloromethane to dimethyl mal-onate in up to 75% yield [393]. The Co(II) complexes are found to be effective for the homogeneous reduction of gem-dichlorocyclopropanes in the presence of anthracene [394]. The formation of the C—C double bond of (258) may be ascribed to the a-elimination of the Co-H species. Thus, benzalchloride (257) can be converted to a mixture consisting primarily of ds- and trans-stilbenes (258) by the action of electrogenerated Co(I)(salen) (Scheme 97) [395-398]. 

Behymer and Hites (1985) determined the effect of different substrates on the rate of photooxidation of anthracene (25 pg/g substrate) using a rotary photoreactor. The photolytic half-lives of anthracene using silica gel, alumina, and fly ash were 1.9, 0.5, and 48 h, respectively. Anthracene (5 mg/L) in a methanol-water solution (1 1 v/v) was subjected to a high pressure mercury lamp or sunlight. Based on a rate constant of 2.3 x lO /min, the corresponding half-life is 30 min (Wang et al., 1991). 

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... 

Fio. 12. Graph illustrating the dependence of the logarithm of retention factor for aromatic hydrocarbons on the carbon load of octadecyl silica bonded phases prepared from Par-tisil with octadecyhrichlorosilane. Mobile phase methanol-water (70 30) eluitest A, benzene A, naphthalene , phenanthrene , anthracene O, pyrene. Reprinted with permission from Herndon t al. (70). 

The acridizinium (benzo[6]quinolizinium) ion, being isoelectronic with anthracene, is fluorescent (55JA4812). The fluorescent quantum yield for acridizinium perchlorate in methanol was reported to be 0.52 (80MI21000). The rate of quenching of this fluorescence by alkyl halides was found to be related to the ionization potential of the halide (78MI21001). Quenching by anions was also measured (79JPR420). 

Although the quinolizinium ion (1), like naphthalene, does not undergo photodimerization, its linear benzo derivative, the acridizinium ion, like anthracene, does so readily (Scheme 27) (57JOC1740). The photodimer dissociates when heated in ethanol. It has been reported that both the dimerization and dissociation in methanol are light-catalyzed and that the quantum yields for the two reactions are 0.23 and 0.49 respectively (78JPR739). 

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