Methylanthracenes

Methylanthracene [613-12-7] M 192.3, m 204-206° Chromatographed on silica gel with cyclohexane as eluent and recrystd from EtOH [Werst 7 i4m Chem Soc 109 32 1987]. 

The low solubility of fullerene (Ceo) in common organic solvents such as THE, MeCN and DCM interferes with its functionalization, which is a key step for its synthetic applications. Solid state photochemistry is a powerful strategy for overcoming this difficulty. Thus a 1 1 mixture of Cgo and 9-methylanthra-cene (Equation 4.10, R = Me) exposed to a high-pressure mercury lamp gives the adduct 72 (R = Me) with 68% conversion [51]. No 9-methylanthracene dimers were detected. Anthracene does not react with Ceo under these conditions this has been correlated to its ionization potential which is lower than that of the 9-methyl derivative. This suggests that the Diels-Alder reaction proceeds via photo-induced electron transfer from 9-methylanthracene to the triplet excited state of Ceo-... 

The decarboxylation of the caesium salt of 9-methylanthracene-10-acetic acid occurs at an even lower potential (0.7 V) and affords the dimer as well as the methyl ether (Eq. 40) [342], The low oxidation potentials for the decarboxylation of 54 (0.13 to 0.77 V) [306a] and 55 (—0.17 V) [306b] indicate too, that the initial electron transfer occurs from the amino or aryl group rather than from the carboxylate. 

The hydrogenation of arenes also has attracted interest, but until recently only a few catalytic systems have been found effective.56-60 The catalytic activity of [Rh(MeOH)2(diphos)]X and of [RuH2(H2)(PPh3)3] in the hydrogenation of 9-trifiuoroacetylanthracene and 9-methylanthracene has been explored.61,62... 

Chemical Name 2-methylanthracene CAS Registry No 613-12-7 Molecular Formula C15H12 Molecular Weight 192.256 Melting Point (°C) ... 

Reported aqueous solubilities of 9-methylanthracene at various temperature and the empirical temperature dependence equations... 

FIGURE 4.1.1.27.1 Logarithm of mole fraction solubility (In x) versus reciprocal temperature for 9-methylanthracene. 

The photo-induced single and double Diels-Alder reactions between [60]fullerene and 9-methylanthracene (212) which gave 213 and 214 were performed in the solid state by Mikami and colleagues (equation 60)141. The Diels-Alder reaction was considered to proceed following a photo-induced electron transfer from 9-methylanthracene to fullerene. The higher ionization potential of anthracene should explain its inreactivity toward the cycloaddition reaction with [60]fullerene. 

Pyrolysis of bis(2-ethylhexyl) phthalate in the presence of polyvinyl chloride at 600 °C produced the following compounds methylindene, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, biphenyl, dimethylnaphthalene, acenaphthene, fluorene, methylacenaphthene, methylfluorene, phenanthrene, anthracene, methylphenanthrene, methylanthracene, methylpyrene or fluoranthene, and 17 unidentified compounds (Bove and Dalven, 1984). 

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