Aromatic acid chlorides table

It seems safe to say that coordination will generally decrease the reactivity of donor atoms in the first row of the periodic table through steric effects. With some reactions the extent of this steric hindrance may be small. Ammonia can be transformed into chloramines when coordinated (34), and aromatic acid chlorides coordinated to A1C13 or TiCl4 may be esterified even when the functional group is a hindered one, as in mesitylene carbonyl chloride (47). These last reactions may proceed through a very reactive carbonium ion, whose existence is rendered possible by the polarization of the ligand which it suffers as a result of coordination. 

Interestingly, only p-nitrobenzoyl chloride reacted with ethyl isocyanoacetate. Other aromatic acid chlorides, including p-chlorobenzoyl chloride, p-fluorobenzoyl chloride, and benzoyl chloride were unreactive even after 15 h at 110°C. This was attributed to marked differences in electrophilicity of the acid chlorides. The authors also considered an alternative mode of cyclization that would have produced 5-substituted 4-oxazolecarboxylic acid esters but found no evidence for these products. Selected examples are shown in Table 1.29. 

Acylation of 2-(trimethylsilyl)oxazoles 1005 and 1008 (X = H) can be effected using acid halides, chloroformates, or oxalates and affords 2-acyloxazoles in poor to good yield (Scheme 1.270 Table 1.76). Only benzoyl chloride was sufficiently reactive among aromatic acid chlorides to acylate 1005 or 1008 (X = H), albeit in low to modest yield. In contrast, benzoylation of 4-methyl-... 

The physical properties of a few tjrpical acid chlorides of aromatic acids are collected in Table IV, 18 7). Some acid anhydrides are also included in this Table (compare Section 111,94). 

Acid Chlorides and Acid Anhydrides of Aromatic Adda, Table IV, 187. Aliphatic Esters, Table III, 106. 

The present procedure4 is an especially effective method for the synthesis of esters of aromatic acids and hindered tertiary alcohols or of acid-labile alcohols such as 2,2-diphenylethanol. The yields are excellent, and the reaction procedure is simple. The method is illustrated by the preparation of /-butyl p-toluate, a compound that could not be prepared by a conventional method0 of esterification involving the acid chloride and /-butanol in the presence of dimothylaniline. Examples of esters prepared by this method are illustrated in Table I. 

FIGURE 3.26. Benzoyl chloride. A. Aromatic C—H stretch, 3065 cm-1. B. The C=0 stretch, 1774 cm-1 (see Table 3.3). (Acid chloride C=0 stretch position shows very small dependence on conjugation aroyl chlorides identified by band such as at C.) C. Fermi resonance band (of C=0 stretch and overtone of 8/2 cm1 band), 1730 cm-1. 

Acid chlorides of aromatic acids, 791 reactions of, 795, 1059 table of, 796 ... 

Table 10.24. Acid chlorides and acid anhydrides of aromatic acids 1351...

Other applications of gas chromatography-mass spectrometry include (Table 16.1) the following polyaromatic hydrocarbons, esters, phenols, aromatic acids, chlorophenols, glycols, hydroxybenzenes, 1 4 dioxane, propiolactone, vinyl chloride,... 

Acid derivatives (esters, acid chlorides, anhydrides, nitriles, and amides) are soluble in common organic solvents such as alcohols, ethers, chlorinated alkanes, and aromatic hydrocarbons. Acid chlorides and anhydrides cannot be used in nucleophilic solvents such as water and alcohols, however, because they react with these solvents. Many of the smaller esters, amides, and nitriles are relatively soluble in water (Table 21-2) because of their high polarity and their ability to form hydrogen bonds with water. 

Acid chlorides are suitable electrophiles. As aromatic and 1-alkenyl halides, bromides and iodides are generally good substrates. Until quite recently, the use of the corresponding chlorides, which are cheaper and often more readily accessible, had been limited to that bearing a strongly electron-withdrawing substituent at a proper position. The use of nickel catalyst [47], bulky phosphine [119], and heterocyclic carbene ligand (Scheme 23, Table 1) [116] enabled aryl chlorides to take part in the reaction. 

Due to the sensitivity of acyl cyanides towards excess cyanide ions it is in general advisable not to use alkali metal cyanides as reagents unless special conditions are secured. Therefore, in most cases cyanides of heavy metals (low concentration of free cyanide) have been applied. These transformations require rather drastic conditions, which restricts the application mainly to the preparation of aromatic acyl cyanides. The latter can be obtained in good yield if copper(I) cyanide is heated with acid chlorides in aromatic solvents for several hours at temperatures of 160 More recent developments are based on the same strategy, but allow the application of milder conditions. In most cases acid chlorides are converted to acyl cyanides. Some reagents and the reaction conditions for their application according to equation (42) are collected in Table 12. 

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