M-Dicyanobenzene

Irradiation of mixtures of 2-alkoxynaphthalenes (R1 = Me, Et or i-Bu) and ammonia or primary amines R2NH2 (R = Me, Et, Pr, i-Pr or CH2=CHCH2) in aqueous acetonitrile containing m-dicyanobenzene gives adducts 152146. 

The photoamination of naphthalene, several substituted naphthalenes, anthracene and phenanthrene with ammonia, methylamine or benzylamine in aqueous acetonitrile in the presence of m-dicyanobenzene gave aminated dihydroarenes, e.g. 155. Secondary amines (dimethylamine and diethylamine) react less efficiently149. 9-Methoxyphenanthrene and... 

The first examples of ortho cycloaddition can be found in a U.S. patent of Ayer and Buchi [1], Benzonitrile and 2-methylbut-2-ene are reported to yield 7,8,8-trimethylbicyclo[4.2.0]octa-2,4-diene-l-carbonitrile upon irradiation under nitrogen with a mercury resonance arc. Similar reactions, all leading to derivatives of bicyclo[4.2.0]octa-2,4-diene-l-carbonitrile occurred when benzonitrile was irradiated in the presence of 2,4,4-trimethylpent-l-ene, ethyl vinyl ether, vinyl acetate, methyl vinyl ketone, and methyl acrylate. The addend pairs para-tolunitrile/oct-l-ene, ort/m-dicyanobenzene/2-methylbut-2-ene, para-dicyanobenzene/but-l-ene, 2,3-dimethylbenzonitrile/propene, and 3,4,5-trimethylbenzonitrile/ethene likewise produced ortho photocycloadducts. 

Yasuda, Pac, and Shima reported the photoamination of aromatic compounds by use of ammonia and primary amines as nucleophiles in the presence of m-di-cyanobenzene as an electron acceptor [30,32], Irradiation of an acetonitrile-water (9 1) solution containing phenanthrene and m-dicyanobenzene in the presence of ammonia or primary amines gives 9-amino-9,10-dihydrophenanthrene deriva-... 

Generation of the radical cation of aromatic substrates in the presence of sodium boron hydride offers another path for reduction, alternative to that via the radical anion seen in Sect. 2.1.2, and, as one may expect in view of the different mechanism, with a different regiochemistry [174-175], Thus, e.g. irradiation of the xylenes in the presence of m-dicyanobenzene and NaBH4 yields the corresponding 1,4-dihydro derivatives rather than the 2,5-dihydro derivatives obtained with dissolved metals [175]. 

Lewis and Petisce [44] have investigated PET reactions between a number of cyano aromatic electron acceptors and electron donating methyl aromatic systems. Botb substitution as well as dimer products have been observed depending on the electron affinity of the acceptor [44,45]. When weak electron acceptors, e.g. m-dicyanobenzene and benzonitrile, were used dibenzyl derivatives were formed predominantly. In contrast, strong electron acceptors produced predominantly substitution products. For example, use of tetracyanobenzene with p-xylene produced predominantly in-cage substitution product while use of m-dicyanoben-... 

The photoamination of aromatic hydrocarbons and arylalkenes by ammonia and primary aliphatic amines occurs via photoinduced electron transfer in the presence of m-dicyanobenzene (Scheme 15) [56-58]. In this photoreaction, secondary amines are less reactive than ammonia and primary amines, and the high concentration of the aminated products retards the photoreaction. This is due to the fact that the oxidation potentials of the aminated products produced by the photoreaction are usually much lower than those of the starting ammonia and primary amines. The secondary amines quench the reactive species much faster than the primary amines. Yasuda extended this photoreaction to intramolecular cyclization reactions [59],... 

Electron transfer dimerization of m-methoxystyrene sensitized by m-dicyanobenzene has been studied and shown to yield the tctralins (198a) and (198b). Dimerizations of this type have been described for the parent... 

Figure 36. Mobility (jj) and its dependence on field strength (E) for TTA (30 wt.%)-doped polystyrene (broken line) and TTA-doped polystyrene containing small amounts of polar additives. Their dipole moments are indicated beside the corresponding lines. The concentration of each additive was 1.3 X 10 molecules cm, corresponding to 2-4 wt. /o p-dinitrobenzene (0.6 D), m-dicyanobenzene (3.6 D), 1-cyanonaphthalene (3.9 D), 3-nitrobiphenyl (4.0 D), o-dicyanobenzene (5.7 D), and 4-r-amylphthalonitrile (6.6 D). (Reprinted with permission from Ref. (56aJ.)...

Cyanobenzonitrile 1,3-Dicyanobenzene m-Dicyanobenzene Dinitrile of isophthalic acid EINECS 210-933-7 HSDB 5724 IPN Isoftalodinltril Isoftalonitrll isophthalodinitrile Isophthalonitrile Nitril kyseliny isoftalove NSC 87860 m-Phthalodinitrile m-Phthalo-dinitrile. Needles mp = 162 bp sublimes d ° = 0.992 XmB221, 227,231,279,287 nm (e= 11500,12000,11100, 532, 570, MeOH) insoluble in petroleum ether, slightly soluble in H2O, soluble in EtzO, CsHe, CHCI3, very soluble in EtOH,... 

Synonyms/Trade Names 1,3-Benzenedicarbonitrlle m-DIcyanobenzene 1,3-Dicyanobenzene Isophthalodinitrile m-PDN ... 

Croonen, Y., Gelade, E., Van der Zegel, M., Van der Auweraer, M., Vanden-driessche, H., De Schryver, F.C., Ahngren, M. Influence of salt, detergent concentration, and temperature on the fluorescence quenching of 1-methylpyrene in sodium dodecyl sulfate with m-dicyanobenzene. J. Phys. Chem. 1983, 87(8), 1426-1431. 

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