Anthra-cene

Pressure (mm. Ho) Water ChLOBO BENZENE Benz- ALDEHYDE Ethyl SALI- CYLATE Glycerol Anthra- cene... 

McMillan DC, PP Fu, CE Cerniglia (1987) Stereoselective fungal metabolism of 7,12-dimethylbenz[a]anthra cene identification and enantiomeric resolution of a K-region dihydrodiol. Appl Environ Microbiol 53 2560-2566. 

Other selected examples include tris(tetramethylethylene diamine-sodium)-9,9-dianthryl 143,154 alkali metal salts of 9,10-bis(diisopropylsilyl)anthracene 144,155 as well as the closely related naked 9,10-bis(trimethylsilyl)anthra-cene radical anion 145.156 This chemistry is further extended to the solvent-shared and solvent-separated alkali metal salts of perylene radical anions and dianions 146, 147,156 while other examples focus on alkali metal salts of 1,2-diphenylbenzene and tetraphenylethylene derivatives, where reduction with potassium in diglyme afforded contact molecules with extensive 7r-bonding, [l,2-Ph2C6H4K(diglyme)] 148.157 Extensive 7r-coordination is also observed in (1,1,4,4 tetraphenylbutadiene-2,3-diyl)tetracesiumbis(diglyme)bis(methoxyethanolate) 149.158... 

Granberg L, Ostergren A, Brandt I, Brittebo EB. 2003. CYPlAl and CYPIBI in blood-brain interfaces CYPIAI-dependent bioactivation of 7,12-dimethylbenz(a)anthra-cene in endothelial cells. Drug Metab Dispos 31 259-265. 

Smooth muscle relaxant activity. Tine-ture of the gland, administered to rabbits, was active on the bladder and intestine " . Toxic effect. Gum, administered orally to adults, was active. A case of methemoglobinemia occurred in a 5-week-old male infant, after administration of asafetida preparation to alleviate colic. Treatment was with intravenous methylene blue and the infant recovered . Tumor-promoting activity. Water extract of the dried oleoresin, administered externally to mice at a dose of 200 pL/animal, was active vs 7,12-dimethylbenz[a]anthra-cene and croton oil treatment ". ... 

Isosteric replacement with fluorine is an effective way to decrease the carcinogenicity of polyaromatic hydrocarbons. For example, 7-methylbenz[o]anthra-cene is highly carcinogenic, but the 1-fluoro analog is not, as the presence of fluoride prevents CYP epoxi-dation at the 1,2-position. 

Fig. 14.14 9,10-Bis(phenylethynyl)anthra-cene (21). (a) structure, showing molecular long axis, (b) columnar arrangement of molecules in the crystal, (c, top) detail showing...

A fairly similar material has been obtained in an FTT synthesis extended over 6 months (Hayatsu et al., 1977). Upon pyrolysis, it gave a mass spectrum resembling that of the Murchison polymer (Fig. 9). The spectrum shows mainly benzene, naphthalene, and their alkyl derivatives, as well as alkyl-indanes, fluorene, anthra-cene/phenanthrene, alkenes, alkanes, and alkylphenols (Hayatsu et al., 1977). This material has not been studied by the more informative, gentle oxidation methods. 

This synthesis is applicable to many aromatic compounds, including alkoxyl or N,N dimethylamino derivatives of benzene and naphthalene, naphthols, indole, and certain reactive hydrocarbons, namely, anthra-cene, 1,2-benzanthracene, 3,4-benzpyrene, ° and pyrene. The high-melting polynuclear hydrocarbons react best in the presence of a solvent, such as o-dichlorobenzene. For example, a solution of anthracene, methyl formanilide, and phosphorus oxychloride in o-dichlorobenzene is heated 1 hour at 90-95° then an aqueous solution of sodium acetate is added, and the solvent and N-methylaniline are removed by steam distillation. The solid residue is readily purified to yield 9-anthraldehyde (84%). With liquid or low-melting compounds a solvent is not required. 

Figure 2. Aromatic compounds reduced to dilithium dianions (A) biphenylene , (B) anthra-cene ", (C) phenanthrene , (D) naphthacene , (E) pentacene , (F) perylene , (G) 9,10-di-phenylphenanthrene, (H) 2,5-diphenylisobenzofuran (I) 2,4,6-lriphenylpyridine. ...

Yoshida, H. (1983). Preputial tumors induced by intragastric intubations of 7,12-dimethylbenz(a)anthra-cene in gonadectomized female and male rats. J Cancer Res Clin Oncol 105, 299-302. 

Sulfonation of anthracene 63 Anthracene is sulfonated by the complex in dioxane almost completely to the 9-sulfonic acid. The equilibrium concentrations depend in a high degree on the temperature a rise in temperature increases the amount of anthracene. However, by controlling the reaction temperature to 40°, sodium anthra-cene-9-sulfonate can be obtained in 70% yield in the reasonable reaction time of 20 hrs. 

Matsubara and Yoshida have shown that 9,10-di(pentafluorophenyl)anthra-cene can be synthesized by a copper-catalyzed arylation of pentafluorobenzene with dibromoanthracene [105], The reaction is only successful if silver oxide base is used. 

Water Purge Phenan- threne 1-Methyl- phenan- threne Anthra- cene 2-Methyl-anthracene... 

The one-step mechanism does not exclude some unbalance in the advancement of bond formation at the transition state. For the reaction of 9-d-anthra-cene and acrylonitrile the addition of the unsubstituted end of the dienophile to the deuterated position of the diene was indeed found to be favoured, the relative rates being l.O . ... 

Sessler. J.L. Sathiosatham, M. Brown, C.T. Rhodes, T.A. Wiederrecht, G. Hydrogen-bond-mediated photoinduced electron-transfer Novel dimethylaniline-anthra-cene ensembles formed via Watson-Crick base-pairing. J. Am. Chem. Soc. 2001, 123 (16), 3655-3660. 

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