Dicarboxylic adds

Azodne-6,7-dicarboxylic add, 1,2-dihydro-1-phenyl-dimethyl ester NMR, 7, 660... 

Naphthalene-1,8-dicarboxylic add, its nitro-substituted derivatives, and naphthalene-1,4,5,8 tetracarboxylic acid, on treatment with sulfur tetrafluoride at 0 C, undergo dehydration to form quantitatively the corresponding anhydrides [218, 221] Unsubstituted and mononitrated monoanhydndes react further at 200-250 °C to give derivatives of 1,1,3,3-tetrafluoro-l// naphtho[I,8 c,d]pyran Dinitronaphthalene-l,8-di-carboxyhc acid anhydndes and naphthalene 1,4,5,8 tetracarboxylic acid dianhydnde give the respective tetra- and octafluoroethers only in the presence of an excess of anhydrous hydrogen fluoride [221] (equabons 113 and 114)... 

In the early stage of thiepin chemistry, Scott26) reported the synthesis of benzo-[phthalaldehyde with diethyl 3-thiapentanedioate followed by hydrolysis. Shortly after Scott s synthesis, Dimroth et al.27) found that the ester 34a was thermally more stable than the free acid... 

Dimethyl tricyclo[4.2.2.02 -5]deca-3,7-diene-9,10-dicarboxylate adds bromine and iodine only to the less hindered double bond to give the syn 1,2-addition product of the cyclobutene moiety79. The product composition from this compound depends on the temperature and the solvent. At high temperatures, the 1,2-addition predominates over the transannular reaction, but this predominance is small in a solvent like chloroform and is lost in a protic solvent such as acetic acid (equation 47). 

Kulprathipanja, S. (1990) Process for the adsorptive separation of hydroxy paraffinic dicarboxylic acids from olefinic dicarboxylic adds. U.S. Patent 4,902,829. 

NMDA, Af-methyl-D-aspartate AMPA, a-amino-3-hydroxy-5-methyl-isoxazole-4-proprionic add 1S,3R-ACPD, L-amino-cydopentane-lS,3R-dicarboxylic add IP3, inosine triphosphate... 

PHTHALIC ANHYDRIDE 1.2- Benzcne-dicarboxylic add anhydride, 1.3- Dioxoplitlialan, PAN, Phtltalandlone NL, III 2 1 0 ... 

Mackowiak, H., and Gottlieb, K. (1998) Ferrocene dicarboxylic add diesters and solid composite propellants containing the compounds. PCT Inti. Appl. WO 9850396. 

Kolbe electrolysis is generally useful for the formation of hydrocarbons from monocarboxylic acids and for the preparation of many difunctional compounds as well. A specific illustration is the synthesis of esters of long-chain dicarboxylic adds from monoesters of appropriate dicarboxylic acids (see p. 33). A number of these syntheses are discussed by Fichter.4 In the present preparation, a two-compartment cell is employed to avoid, or at least greatly reduce, undesired reduction of the nitro group at the cathode. It seems likely that the procedure could be adapted to the preparation of other difunctional compounds containing groups that are easily reduced. 

Paramagnetic shifts may be induced in cations which associate with suitable lanthanide complexes. Thus in aqueous solution, [M(hpda)3]6, where M = Dy or Tm and H3hpda = 4-hydroxypyridine-2,6-dicarboxylic add, associates with Mg2-1, 39K+, 23Na+, 87Rb+ or 14NH4 and produces shifts of up to 25 p.p.m. which are most marked above pH 7.582 A similar effect is shown for cations (and anions and uncharged molecules) by lanthanide tetra-p-sulfonatophenyl-porphyrins in aqueous solutions.583 This is discussed in Section 39.2.6.3, as are the large shifts produced in aqueous solution by Na[Eu(dota)(H20)] (H4 dota = 23).584... 

Cyclizative condensations based on aldol-type reactions which conform to the llbd pattern have also been developed. Condensation of bis(alkoxycarbonylmethyl)amines or bis(cyanomethyl)amines with benzil affords 3,4-diarylpyrrole-2,5-dicarboxylic add esters or nitriles. These reactions frequently lead to partial hydrolysis of at least one of the alkoxycarbonyl substituents and if the 3,4-diarylpyrrole is the ultimate objective, work-up involving complete hydrolytic decarboxylation is appropriate (equation 119) (6lLA(639)l02, 65JOC859). 

The protonation of oxepins-arene oxides at the ring oxygen atom and subsequent acid-catalyzed isomerization are very dependent upon the nature of substituents on the ring. This is exemplified by a comparison of the relative stabilities of oxepin (7) and oxepin-2,7-dicarboxylic add (18) under add conditions. Thus oxepin (7) spontaneously decomposed on clean glassware at ambient temperature (unless prewashed with base) while (18) showed no change over a period of 10 days in trifluoroacetic add (79JA2470). 

The most common reaction of this type is the cyclization of various derivatives of hydrazine and substituted hydrazines with pyridine o-dicarboxylic adds and related compounds. Reactions in which the acid derivative reacts directly with the hydrazine are dealt with as [4 + 2] reactions in Section 2.15.10.6.1. 

Diaminopyridazino[4,5-d]pyridazine is prepared by the condensation of 4,5-dicyanopyridazine with hydrazine (68JHC53). In like manner, condensation of the pyridazine-4,5-dicarboxylic esters (157) with hydrazines gives the corresponding pyridazino[4,5-d]-pyridazine-l,4-(2f/,3f/)-diones (158). These compounds can also be prepared by condensing pyridazine-4,5-dicarboxylic add anhydrides with hydrazines (75JHC95). 

Eoreon and Suzuki18 8 carried out the hydration of ezo-1,2-epoxy l.icydo 2.2.1]oct ne aro-4,C dicarboxylic add, and isolated a lactone i unloved to bo thoskoletal rearrangement product depicted in Eq. (636b). 

FIGURE 12. Chains of H-bonded molecules of (a) cis- (63c) and (b) International Union of Crystallography from Reference 112... 

The reactions of oxalic add, including the formation of normal and add salts and esters, are typical of the dicarboxylic adds class. Oxalic add, however, does not form an anhydride. 

Benzo[6]thiophene-2,3-dicarboxylic add dimethyl ester synthesis, 4, 895... 

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