Carboxylic acid table

The customary method for the laboratory synthesis of acid anhydrides is the reac tion of acyl chlorides with carboxylic acids (Table 20 1)... 

Carboxylic acids with a halide, hydroxy or amino group in the a-position form no dimers (Table 2, No. 11), except when two or three fluorine atoms are pr ent there (Table 2, No. 12). A large amount of work has been devoted to the coupling of fluoro-carboxylic acids (Table 2, Nos. 13-16) due to interesting properties of the produced fluorohydrocarbons. By statistical analysis optimal conditions for Kolbe ela trolysis of perfluorinated acids have been calculated [135]. 

I he present procedure, a modification of one reported earlier by ilie submitters," has been applied to the a-chlorination of a scries of aliphatic carboxylic acids (Table I). In these reactions... 

Trost and coworkers have devised a stereocontrolled 1,3-diene synthesis employing a palladium-catalysed decarboxylative elimination procedure from allylic acetates carrying carboxylic acid functionality ji- to the acetate group (equation 18)48. This decarboxylative elimination strategy has been applied to the synthesis of an insect pheromone, codlemone48a and the ethyl ester of vitamin A carboxylic acid (Table 5)48b. 

Resin-catalysed esterification of carboxylic acids (Table 3.10)... 

From Nocardia strains several closely related compounds (nocobactins, formo-bactin, amamistatins) were isolated that contain three typically Fe " binding sites, two hydroxamate units, and ahydroxyphenyloxazole stmcture (cf. Sect. 3.2 below). The C-terminus is A-hydroxy-cyc/o-Lys bound to a long chain 3-hydroxy fatty acid, whose hydroxy group is esterified by A -acyl-A -hydroxy-Lys, the a-amino group of which is bound to 2-o-hydroxyphenyl-5-methyl-oxazole-4-carboxylic acid (Table 4). For the amamistatins the configuration of the cyclic lysine was determined as L, the open one as d, and that of C-3 of the fatty acid as (S). The involvement in the iron metabolism was not investigated. 

This is one of the most important applications for RuO. Oxidative cleavage of alkenes and alkynes by a variety of reagents has been reviewed [30, 35, 50, 60, 68-71]. The gentler cleavage reactions of alkenes to aldehydes or ketones are considered first (Table 3.3), then the commoner cases of cleavage to carboxylic acids (Table 3.6). 

In their acidity 3-acyltetramic acids resemble carboxylic acids (Table II). 

A 16,000-member library was synthesized using this procedure. Twenty-one halonitrobenzenes were combined with 20 halides and half were converted to the sulfone, resulting in 840 3-amino-l,5-benzothiazepine derivatives. These were then reacted with 19 carboxylic acids. Table V shows a representative example of the reagents used. A small random sample of 480 compounds from the library was analyzed by HPLC/MS. Figure 4 shows the purity distribution for the library. Most of the compounds were prepared in high purity. 

The Bashkirov oxidation (liquid-phase oxidation of n-alkanes or cycloalkanes in the presence of boric acid and hydrolysis) yields the corresponding secondary alcohols [16, 17]. The reaction is used industrially for oxidation of C10 to C18 n-alkanes, providing raw materials for detergents and for oxidation of cyclododecane to cyclo-dodecanol as an intermediate for the production of Nylon 12 (Table 1, entry 8). The process is not of much commercial importance in the western world, however. Oxidation in the absence of boric acids usually leads to mixtures of alcohols, ketones, and carboxylic acids (Table 1, entry 9). 

Recently, Anton et al. have proposed, from the analysis of the carbon-13 NMR spectra, that the tentatively identified cyanoco-balamin-fo-, -e-, and -d-carboxylic acid (Table II) should be cyanoco-balamin d-, and - -carboxylic acid, respectively (40). 

Consequently there appears to be a sound empirical basis for the use of the OTs scale of solvent ionizing power. Its use should be restricted to sulphonates, however, because of the differential effects of electrophilic solvation in acidic solvents (see Section 4). The importance of these effects can be seen by comparing the Y and Iqxs values for carboxylic acids (Table 5) it appears that, relative to 80% ethanol/water, a carboxylic acid ionizes a tosylate about ten times more rapidly than a chloride. 

Common names of aldehydes are derived from the common names of the corresponding carboxylic acids (Table 18-2). These names often reflect the Latin or Greek term for the original source of the acid or the aldehyde. Greek letters are used with common names of aldehydes to give the locations of substituents. The first... 

Phenols must therefore be considerably stronger acids than water, but considerably weaker acids than the carboxylic acids. Table 24.1 (p. 788) shows that this is indeed so most phenols have KaS of about 10 whereas carboxylic acids... 

---