Chrysene, preparation

CHROMIUM TRIOXIDE-PYRIDINE COMPLEX, preparation in situ, 55, 84 Chrysene, 58,15, 16 fzans-Cinnamaldehyde, 57, 85 Cinnamaldehyde dimethylacetal, 57, 84 Cinnamyl alcohol, 56,105 58, 9 2-Cinnamylthio-2-thiazoline, 56, 82 Citric acid, 58,43 Citronellal, 58, 107, 112 Cleavage of methyl ethers with iodotri-methylsilane, 59, 35 Cobalt(II) acetylacetonate, 57, 13 Conjugate addition of aryl aldehydes, 59, 53 Copper (I) bromide, 58, 52, 54, 56 59,123 COPPER CATALYZED ARYLATION OF /3-DlCARBONYL COMPOUNDS, 58, 52 Copper (I) chloride, 57, 34 Copper (II) chloride, 56, 10 Copper(I) iodide, 55, 105, 123, 124 Copper(I) oxide, 59, 206 Copper(ll) oxide, 56, 10 Copper salts of carboxylic acids, 59, 127 Copper(l) thiophenoxide, 55, 123 59, 210 Copper(l) trifluoromethanesulfonate, 59, 202... 

The compound I O.i. I Ob-dihydro-5//, 12//-4b,5,6,12-tetraaza-chrysen-l ] -one 81 <2003JHC357> was prepared through diazotization of the corresponding amine derivative 3-(2-aminophenyl)-l//-quinoxalin-2-one 78. The reaction proceeded through intermediates 79 and 80 (Scheme 4). 

Epoxidation of aromatic hydrocarbons is an important method for the preparation of arene oxides. m-Chloroperbenzoic acid (MCPBA) is used in a two-phase system that involves treating the hydrocarbon with a large excess ( 10-fold) of MCPBA in methylene chloride-aqueous sodium bicarbonate at room temperature. The yields are moderate (10-60%). Because the arene oxides are sensitive to acids, the presence of sodium bicarbonate buffer is necessary. A number of K-region (see Section VII for a definition) epoxides like phenanthrene 9,10-oxide (1, 59%), 9,10-dimethylphenanthrene 9,10-oxide (2,40%), 9-phenylphenanthrene 9,10-epoxide (3,50%), pyrene 4,5-oxide (4, 14%), and chrysene 4,5-oxide (5,9%) have been prepared by this method.9... 

Many polycyclic aromatic amines and aldehydes are commercially available, but their supply is very limited. Preparation of these starting materials is necessary for studying the (3-lactam formation reaction [93]. Nitro compounds are the precursors for the amines. An important task was to prepare polycyclic aromatic nitro compounds, particularly those of chrysene, phenanthrene, pyrene, and dibenzofluorene in good yield. Nitration of these hydrocarbons with concentrated nitric acid in sulfuric acid is a widely used reaction for this purpose. Our research culminated in facile synthesis of polyaromatic nitro derivative 9 starting from polyaromatic hydrocarbons (PAHs) 8 through the use of bismuth nitrate impregnated with clay (Scheme 1) ([94, 95] for some examples of bismuth nitrate-catalyzed reactions... 

In vitro rat liver and mouse skin preparations have been reported to metabolize chrysene to its 1,2-, 3,4-, and 5,6-dihydrodiols and to some monohydroxy... 

Three tetracyclic systems, triphenylene, benz(c)phenanthrene and chrysene can be derived by angular benzannelation of phenanthrene and hence these hydrocarbons may be synthesized from corresponding phenanthreneacetonitriles. The phenanthrene-1-acetonitrile (81) used for the preparation of the chrysenes (82) was obtained from phenanthrene-l-carbonitrile (72a) in a sequence of conventional steps hydrolysis to the acid (84%) by KOH in triglycol, reduction to the carbinol (82%) by sodium dihydrido-bis(methoxyethoxy)aluminate, conversion by thionyl chloride in benzene to the chloromethyl derivative (98%), and finally reaction of the latter with sodium cyanide in DMSO to (81) (94%). 

Numerous aromatic compounds including several bowl-shaped fullerene fragments have been prepared by this method, e.g. cyclopenta[z/]fluoranthene (22, Scheme8, [54d,56a]), cyclopenta[bc]corannulene (23, [55a]) and diace-naphtho[3,2,l,8-cdejg 3, 2, l, 8 -Zmnop]chrysene (24, see Scheme 9, [55b,c]). Of special importance is this approach for the synthesis of cyclopenta-annelated PAHs, e.g. and the three isomeric dicyclopentapyrenes (25-27, Scheme 9, [54e, 56b]). Using these reference samples, several cyclopenta-annelated PAHs could be identified as byproducts formed in the incomplete oxidation of hydrocarbons in fuel rich flames [57]. 

Sample preparation 5 g Ointment containing 1% clotrimazole + 70 mL MeOH, sonicate for 15 min, make up to 100 mL with MeOH, filter (0.22 xm FIFE), mix an aliquot of the filtrate with an equal volume of 6 p,g/mL chrysene in MeOH, iiyect a 20 p,L aliquot. 

Hydrogenation over a mixed Pd/C-PtOa catalyst affords the hexahydrochrysene 2. This product can be dehydrogenated by DDQ to 3,4,5,6-tetrahydrochrysene(3), which has been used to prepare the anti-Aio epoxide 4, of interest as a possible carcinogenic metabolite of chrysene. ... 

Reversed-phase EC on chemically bonded Cig (octadecylsilane) stationary phases is by far the most popular liquid chromatographic mode for separation of PAH compounds. Resolution is greatly influenced by the type of synthesis used to prepare the bonded phase. Good resolution can be achieved for the 16 US EPA PAHs on polymeric Cig phases. However, some isomers are unresolved (chrysene and benzo[a] anthracene) or only partially resolved [htmo ght perylene and indeno[l,2,3-cd]pyrene, benzo[ ]fluor-anthene, and benzo[ ]fluoranthene, or fluoranthene and acenaphthene) when monomeric Cig phases are used. 

Laurent summarised the experiments which had been made on the action of nitric acid on aromatic hydrocarbons, and prepared nitro-derivatives of naphthalene, anthracene, chrysene and pyrene. In a table he arranged them in decreasing order of the numbers of equivalents of carbon, beginning with anthracene and ending with phene (benzene) He continued to... 

In a similar effort, the BN for C C isosteric replacement niitnic 95 of dibenzo, p]chrysene was prepared in several steps from bis(biphenyl-2-yl) amine and its X-ray crystal structure determined for a direct comparison with that of the parent PAHs (Scheme 30) (201 IJAl8614). A condition-variation study of the last step revealed that 4 equivalents of Lewis acid AICI3 and 1.5 equivalents of the additive 2,2,6,6-tetramethylpiperidine... 

---