2,2-Diphenic acid

Many diazonium compounds when treated with an ammoniacal cuprous Formerly known as Diphenic acid. 

Alkaline permanganate. Heat under reflux i g. of i,2 naph thoquinone, 50 ml. of saturated aqueous KMn04 solution and 2 g. of anhydrous NajCO for 30 minutes. Then proceed as for oxidation of benzyl chloride (p. 393). 1,2-Naphthoquinone gives phthalic acid, m.p. 195°. Phenanthraquinone gives diphenic acid, HOOC CeH CeH COOH, m.p. 229°. 

Diphenic acid. Phenanthrene upon oxidation in acetic acid solution at 85° with 30 per cent, hydrogen peroxide gives diphenic acid (diphenyl-2 2 -di-carboxyHc acid) no phenanthraquinone is formed under these experimental conditions. The reaction is essentially an oxidation of phenanthrene with peracetic acid. (For another method of preparation, see Section I V,74.)... 

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). 

Dinitro-6,6 -diphenic acid can actually be resolved into two enantiomeric forms, but heating the samples causes them to racemize. Explain. 

Diphensiiure, /. diphenic acid. Diphenyl-arsenchloriir, n. diphenylarseni oua chloride (chlorodiphenylarsine). -borchlorid, n, diphenylboron chloride, -schwarz, n. diphenyl black,... 

Diphenic acid (H2A) also forms diorganotin(IV) complexes, which are with two monodentate -COO groups. On the other hand, soluble dinuclear triorganotin(IV) complexes (where the organo moieties are Me and Ph) contain symmetrically bound carboxylates, while the less-soluble compound (cHexsSn) has two asymmetrically bonded carboxylates. All have Tbp structures with [RsSnirV)] units remote from each other. °... 

An interesting coupling reaction with the diazonium salt derived from anthranilic acid leads to an excellent method for the preparation of diphenic acid. The reaction occurs with cuprous salts in ammoniacal solution y /COOH 2JJC1 y yCOOIl 2Cu+... 

Diphenic Acid.—The analysis of this compound is not complete. The results obtained show that the crystal is orthorhombic with the dimensions a = 14.12, b = 11.90, c = 13.75, and that there are eight molecules in the unit cell. This indicates an arrangement quite different from the other compounds studied as the unit cell is approximately half as long in one dimension and twice as wide in the other two. It is possible that this is caused by the attraction and consequent doubling of COOH groups such as is found in the case of aliphatic compounds. 

Other compounds now being investigated are difluoro-diphenic acid, hexachloro-diphenyl, octamethyl diphenyl, diphenyl benzene. Thanks are due Professor Roger Adams for suggesting this research and for providing the necessary materials. 

CD and ORD measurements are a useful tool in studying configuration and conformation. The configuration of optically active 4,4 -dicarboxy-2,2, 5,5 -tetramethyl-3,3 -biselenienyl (1, X = Se) relative to its thiophene analog (1, X = S), was determined by reducing both to the corresponding 4,4 -dihydroxymethyl derivatives (2), which could be related to each other by the quasi-racemate method and by circular dichroism studies.15 Compounds 1 have also been related to 3,3, 6,6 -tetramethyl-2,2 -diphenic acid (3), and it was found that the levorotatory form of 1 (X = Se, S) and the dextrorotatory form of 3 have the -configuration.16... 

Diphenoyl peroxide is the cyclic peroxide of diphenic acid (2,2 -biphenyldicar-boxylic acid) (Fig. 7). It undergoes thermal decomposition to form 3,4-benzocou-... 

Diphenic acid, bl41 Diphenolic acid, b205 Diphenyl, bl38 Diphenylacetone, d767 Diphenylbenzenes, t7 thru t9 sym-Diphenylcarbazide, d746 Diphenyldiazene, a312... 

The heterocyclic acylphosphines (52) and (53) have been prepared by the reaction of phenylbis(trimethylsilyl)phosphine with the acid chlorides derived from phthalic and diphenic acids. The reaction of 2,3-dichloromaleic anhydride or thioanhydride with phenylbis(trimethylsilyl)phosphine gives derivatives of the 1,4-dihydro-p-diphosphorin system (54).45... 

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