Nitration of anthracene

The nitration of anthracene is more difficult to perform and is not recommended as a test. 

It is probable that the nitration of anthracene with nitric acid in 7-5 % aqueous sulpholan proceeds through the rapid formation of a complex. ... 

Both phenanthrene and anthracene have a tendency to undergo addition reactions under the eonditions involved in eertain eleetrophilic substitutions. For example, in the nitration of anthracene in the presence of hydrochloric acid, an intermediate addition product can be isolated. This is a result of the relatively close balance in resonance stabilization to be regained by elimination (giving an anthracene ring) or addition (resulting in two benzenoid rings). 

Nitroanthrone has been prepared by the nitration of anthracene in isobutyl alcohol,1 and by the nitration of anthrone.2... 

Note Nitration of anthracene is discussed in the following papers ... 

The procedure described is a modification of that of Dimroth.8 9-Nitroanthracene has also been prepared by nitration of anthracene with copper nitrate in glacial acetic acid and with diacetyl-orthonitric acid.4 Other methods include direct nitration in acetic acid solution with nitric acid and acetic anhydride.6... 

Cerfontain and Telder [48] acquired an indication of the possible reversibility of aromatic nitration of anthracene-9-d, and finally Olah and associates [49] obtained evidence of the reversibility of the nitration of 9-nitroanthracene and pentamethylnitrobenzene when they found that these substances catalysed by superacids can yield nitrobenzene, nitrotoluene and nitromesytylene when reacted with benzene, toluene and mesitylene respectively. They suggested the mechanism as follows ... 

Although nucleophilic substitution of 3-halo-1,2,5-thiadiazoles is known, the symmetry of the heterocyclic nucleus prevents the detection of the aryne 567 by cine-substitution in the absence of isotopic labeling. An attempt to trap this species with anthracene (147) from the aprotic diazotization " of the amino acid 568 gave, instead of the heterotriptycene 569, a mixture of 9-nitro- (341) and 9-thiocyanoanthracene (570). The former compound is also observed in a similar reaction in the thiophene series (Section III.3.A.d) and could arise by direct nitration of anthracene with nitrous acid " present in the alkyl nitrite. 

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