U Carboxylic Acids

Acid Anhydrides. Acid anhydrides react with alcohols to form esters (in high yields in many cases) with u carboxylic acid formed as by-product ... 

The preparation and structure of homoannular diacetyl ferrocenes 164), and intramolecular cyclizations, both homoannular 168) and heteroannular I48, 168), have been exhaustively investigated. As part of this work, ferrocene carboxylic acids have been prepared 170). A rearrangement with ortho-substitution of a quaternary ammonium ion derived from ferrocene is also noteworthy 99). Work has been done on the isolation of optical isomers of substituted ferrocene derivatives 6, 166) and on cis-trans isomerism 169). 

HDPE, 231J, control 925 HDPE + TiO2 (2.3%) 6U HDPE + anthraquinone 385 HDPE + anthrone 20 HDPE + benzanthrone 20 HDPE + 2-methylanthraquinone 50 HDPE + 1,3,5-triacetylbenzene 50 HDPE + a-bromo- -phenylacetophenone 75 HDPE + 9-fluorenone-U-carboxylic acid 575 HDPE + flavone 650... 

Fig. 43.5). Two oxidative metabolites also have been isolated, with the major oxidation product being the u)-carboxylic acid (31). Side effects with oseltamivir are minor, consist of nausea and vomiting, and occur primarily in the first two days of therapy. 

Some of the physical properties of fatty acid nitriles are Hsted in Table 14 (see also Carboxylic acids). Eatty acid nitriles are produced as intermediates for a large variety of amines and amides. Estimated U.S. production capacity (1980) was >140, 000 t/yr. Eatty acid nitriles are produced from the corresponding acids by a catalytic reaction with ammonia in the Hquid phase. They have Httie use other than as intermediates but could have some utility as surfactants (qv), mst inhibitors, and plastici2ers (qv). 

Branched-Chain Saturated Acids" under "Eatty Acids (Branched-Chain)" in ECT 1st ed., VoL 6, pp. 259—262, by M. D. Reiner (in part), and J. A. Eield (in part). Union Carbide and Carbon Corp. "Branched-Chain Acids" under "Eatty Acids" in ECT 2nd ed., VoL 8, pp. 849—850, by W. C. Ault, U.S. Department of Agriculture "Branched-Chain Acids" under "Carboxylic Acids" in ECT 3rd ed., Vol. 4, pp. 861—863, by R. W. Johnson, Jr., Union Camp Corp. 

Methylthio-4//-pyrido[l,2-u]pyrimidin-4-one was prepared by FVT of 2-methylthio-4-oxo-4//-pyrido[l, 2-u]pyrimidine-3-carboxylic acid at 650 °C at 8 X 10 -nbar for 4h (99JCS(P2)1087). 

Fischer indolization of 9-arylhydrazono-6,7,8,9-tetrahydro-4//-pyrido-[l,2-u]pyrimidin-4-ones 289 by heating in 85% phosphoric acid, or in PPA yielded 7,12-dihydropyrimido[l, 2 l,2]pyrido[3,4-Z)]indol-4(6//)-ones 290 (96JHC799, 99MI12, 00MI22). From the 3-ester and 3-carboxylic acid derivatives 289 (R = COOEt, COOH) and decarboxylated products 290 (R = H) were obtained. 

Lithiation of 2-(2-alkylphenyl)-l,2,3,4-tetrahydropyrimidines 427 with 1.3 M BuLi in the presence of A/, A/, A, A -tetramethylethylenediamine, then with 1.3 M -BuLi, followed by the addition of a carboxylic acid methyl ester, and treatment of the reaction mixture with pTSA afforded 3,4-dihydro-2/f-pyrimido[2,l-u]isoquinolines 428 after chromatographic work-up (98JMC1050). 

Trihydroxy-2,3-dihydro-l//-pyrimido[l,2-u]quinoline-3-car-boxylic acid and (420) and its (15)-1-carboxylic acid isomer were isolated from isopyoverdins (97ZN(C)549, 01T1019) and pyoverdins (99MI27), respectively, after acidic hydrolysis in 3 M HCl for 5 days at 110°C. 

ZN(C)153, 00ZN(C)323, 00ZN(C)857, 01MI2, 01MIP4, 01TL5849). 5-Amino-8,9-dihydroxy-2,3-dihydro-l//-pyrimido[l,2-u]quinoline-3-carboxylic acid moiety 4 was also identified as a chromophoric moiety of certain... 

Amine bound to a Wang-polystyrene resin 381 was acylated with 4-oxo-4Ff-pyrido[l,2-u]pyrazine-3-carboxylic acid in the presence of bromotrispyrrolidinophosphonium hexafluorophosphate and /-Pr2NEt in A-methylpyrrolidone (98MIP16). l-(4-Cyclohexyl-4-r / r-butylaminocarbo-nyl-l-piperidyl)-2-(4-fluorophenyl)ethylamine was acylated with perhydro-pyrido[l,2-u]pyrazine-3-carboxylic acid (01MIP19). An amino group of a macrocyclic compound attached to a solid support was acylated with... 

To 11.0 grams of 3-methylf avone-8-carboxylic acid chloride dissolved in 150 ml of anhydrous benzene is added at room temperature 4,8 grams of piperidinoethanol and the mixture refluxed for 2 to 3 hours. The separated solid is filtered, washed with benzene and dried. The product, piperidinoethyl 3-methylflavone-8-carboxylate hydrochloride is obtained as a colorless crystalline solid, MP 232° to 234°C, (from U.S. Patent 2,921,070),... 

Although lithium aldolates generally display a rather moderate preference for the u/f/z-isomer4, considerable degrees of diastereoselectivity have been observed in the reversible addition of doubly deprotonated carboxylic acids to aldehydes20. For example, the syn- and uw/z-alkox-ides, which form in a ratio of 1.9 1 in the kinctically controlled aldol addition, equilibrate in tetrahydrofuran at 25 C after several hours to a 1 49 mixture in favor of the anti-product20. 

A completely different dipolar cycloaddition model has been proposed39 in order to rationalize the stereochemical outcome of the addition of doubly deprotonated carboxylic acids to aldehydes, which is known as the Ivanov reaction. In the irreversible reaction of phenylacetic acid with 2,2-dimethylpropanal, metal chelation is completely unfavorable. Thus simple diastereoselectivity in favor of u f/-adducts is extremely low when chelating cations, e.g., Zn2 + or Mg- +, are used. Amazingly, the most naked dianions provide the highest anti/syn ratios as indicated by the results obtained with the potassium salt in the presence of a crown ether. 

Actinide complexes with carboxylic acids. U. Casellato, P. A. Vigato and M. Vidali, Coord. Chem. Rev., 1978, 26, 85-159 (276). 

Elder DJE, P Morgan, DJ Kelly (1992) Anaerobic degradation of tra -cinnamate and u-phenylalkane carboxylic acids by the photosynthetic bacterium Rhodopseudomonas palustris evidence for a beta-oxidation mechanism. Arch Microbiol 157 148-154. 

The reaction between 60% HNO3, octanol, and 3-bromo-2,3-dimethyl propanol proceeds slowly under mechanical stirring at room temperature and gives quantitative yields of the nitrate only after 12 hours. By contrast ultra-sonochemistry (u/s) gives quantitative yields of carboxylic acids in just 20 minutes at room temperature (Pestman et al., 1994). 

The heats of ionisation and neutralisation of amino and hydroxylic bis and tris phosphonic acids have been investigated.253 Calorimetry in combination with u.v. and n.m.r. spectroscopy uas used to study the adducts of fluoroalkyl carboxylic acids with diethyl phosphonate.254 The heats of formation of the t-butoxytriphenylphosphoranyl radical uas consistent with the phosphonium structure (92).255 There has been a thermal analysis of the adducts of phosphonic and phosphoric acids with... 

The geometric nature of the problem is posed by the very structure of a carboxylic acid 4. If two, or even more, of such functions are to converge on a single basic site, the least one can anticipate is that a U-turn must be engineered into the system. This arises from the direction of the carbonyl-C, bond which points in a direction roughly opposite to the direction indicated by the OH bond. From this perspective, the tricarboxylic acid 5 a first described by Kemp 8) offers an unusually favorable architecture. In this, three methyls force the smaller carboxyl groups to assume a triaxial... 

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