Diphenyl-9,10-dihydroanthracene

Examples include luminescence from anthracene crystals subjected to alternating electric current (159), luminescence from electron recombination with the carbazole free radical produced by photolysis of potassium carba2ole in a fro2en glass matrix (160), reactions of free radicals with solvated electrons (155), and reduction of mtheiiium(III)tris(bipyridyl) with the hydrated electron (161). Other examples include the oxidation of aromatic radical anions with such oxidants as chlorine or ben2oyl peroxide (162,163), and the reduction of 9,10-dichloro-9,10-diphenyl-9,10-dihydroanthracene with the 9,10-diphenylanthracene radical anion (162,164). Many other examples of electron-transfer chemiluminescence have been reported (156,165). 

Applied to the synthesis of hydrocarbons the following results have been obtained by this new method. 9 10-Diphenyl-9 10-dihydroanthracene is formed by the condensation of benzene and chloroform, whilst in the ordinary Friedel-Crafts reaction (A., 194, 254 227, 107) triphenyl-methane (Preparation 6) is the main product, traces of chlorarylmethanes and tetraphenylethane (B., 26, 1952) being also formed. The same compound is also obtained from benzal chloride and benzene. Carbon tetrachloride and benzene give 9 9 10 10-tetraphenyl-9 10-dihydroanthracene as do also phenylchloroform and benzene. In the older reaction triphenylchloromethane (p. 432) is the chief product. 

Chloroform and toluene yield by this process dimethyl-9 10-ditolyl-9 10-dihydroanthracene using aluminium chloride, tetratolylethane is obtained (B., 14, 1530). Benzylidene chloride and toluene yield dimethyl-9 10-diphenyl-9 10-dihydroanthracene. 

Csoregh, L, Brehmer, T, Bombicz, P. and Weber, E. (2001). Halogen... halogen versus OH... O supramolecular interactions in the crystal structures of a series of halogen and methyl substituted cw-9,10-diphenyl-9,10-dihydroanthracene-9,10-diols. Cryst. Eng. 4, 343-57. [272]... 

Bond, D.R. Caira, M.R. Harvey. G.A. Nassimbeni. L.R. Complexation with diol host compounds. 5. Structures and thermal analysis of inclusion compounds of rra i-9.10-dihydroxy-9.10-diphenyl-9.10-dihydroanthracene with 2-butanone. 4-vinylpyridine, 4-methylpyridine and 2-methyl-pyridine. Acta Crystallogr. 1990. B46. 771-780. 

Model compound studies were also carried out in MeOH/KOH, and the results are shown in Table VI. Phenanthrene and biphenyl were quantitatively recovered unchanged by the reactions, and bibenzyl was recovered in 95% yield, with small amounts of toluene observed. Anthracene and diphenyl ether, on the other hand, were converted respectively to 9,10-dihydroanthracene and a mixture of polymethyl-phenols similar to that observed in the work with coal. The cleavage of diphenyl ether via hydrogenolysis should yield both benzene and phenol as products we saw no benzene in our study, and our... 

Data for the related compounds 9,9-diphenyl-9-germafluorene and 9-oxa-10-dichlorogermyl-9,10-dihydroanthracene, are, however, less easily interpreted. Ring planarity is forced upon the fluorene derivative by the absence of a bridging atom at the 9 position of the anthracene skeleton, thereby affording the most favorable molecular architecture for heteroatom it bond participation. Contrary to expectation, however, the exocyclic Ge—C bonds are shorter than the endocyclic analogs (Table III), casting doubt upon the reliability of the data (68). 

We have already mentioned that l,3-diphenyl-l,3-dihydrobenzo-[c]thiophene 2,2-dioxide gives 9-phenyl-9,10-dihydroanthracene as the major product [Eq. (6)] on being heated. Unlike 1,3-dihydro-... 

UV-Vis, H and NMR study of monometallic salts of 9,10-dihydroan-thracene and its 9,10-disubstituted derivatives in THE, showed lithium 9-phenyl-9,10-dihydroanthracene-9-ide, lithium 9,10-dimethyl-9,10-dihydroanthracenide and lithium 9,10-diphenyl-9,10-dihydroanthracenide exist as a solvent separated ion pair (SSIP). Sodium, potassium, rubidium and cesium 9,10-dihydroanthracenides, 9-methyl-9,10-dihydroanthracene-10-ides and 9-cyano-9,10-dihydroanthracenides exist as contact ion pairs (CIP) in solution. A model, taking into account the geometry and charge distribution, for the transition of CIP of alkali metal salts of 9,10-dihy-droanthracene and its derivatives into SSIP is proposed [283]. 

Fig. 11 Plot of obs versus guest pressure for the enclathration of acetone vapor by fra 5-9,10-dihydroxy-9,10-diphenyl-9T0-dihydroanthracene. Note the existence of threshold pressures at both temperatures.

Condensed p-quinones. 2,3-Dihydroanthracene-l,4-dione in dimethyl sulfoxide added under Ng and anhydrous conditions to a cold mixture of phthalaldehyde and a soln. of Na-methoxide in methanol, and stirred 6 hrs. at room temp. -> pentacene-6,13-quinone. Y 77%. - Similarly with l,3-diphenyl-5,6-dihydro-isobenzofuran-4,7-dione l,3-diphenylanthra[2,3-c]furan-4,ll-dione. Y 50%. F. e. s. A. Verine, Y. Lepage, and B. Casteignau, Bl. 1973, 1154. 

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