Carboxylic acid anhydrides reactions

Friedel-Crafts acylation of aromatic compounds (Section 12 7) Acyl chlorides and carboxylic acid anhydrides acylate aromatic rings in the presence of alumi num chloride The reaction is electrophil ic aromatic substitution in which acylium ions are generated and attack the ring... 

Amines are convert ed to amides on reaction with acyl chlorides Other acylating agents such as carboxylic acid anhydrides and esters may also be used but are less reactive... 

The alcohol groups of carbohydrates undergo chemical reactions typical of hydroxyl functions They are converted to esters by reaction with acyl chlorides and carboxylic acid anhydrides... 

Step 2 Structurally O acylisoureas resemble carboxylic acid anhydrides and are powerful acylatmg agents In the reaction s second stage the amine adds to the carbonyl group of the O acylisourea to give a tetrahedral intermediate... 

By virtue of their fused /3-lactam-thiazolidine ring structure, the penicillins behave as acylating agents of a reactivity comparable to carboxylic acid anhydrides (see Section 5.11.2.1). This reactivity is responsible for many of the properties of the penicillins, e.g. difficult isolation due to hydrolytic instability (B-49MI51102), antibacterial activity due to irreversible transpeptidase inhibition (Section 5.11.5.1), and antigen formation via reaction with protein molecules. 

Similar additions have been successfully carried out with carboxylic acids, anhydrides, acyl halides, carboxylic esters, nitriles, and other types of compounds. These reactions are not successful when the alkene contains electron-withdrawing groups such as halo or carbonyl groups. A free-radical initiator is required, usually peroxides or UV light. The mechanism is illustrated for aldehydes but is similar for the other compounds ... 

In addition to acyl halides and acid anhydrides, there are a number of milder and more selective acylating agents that can be readily prepared from carboxylic acids. Imidazolides, the (V-acyl derivatives of imidazole, are examples.115 Imidazolides are isolable substances and can be prepared directly from the carboxylic acid by reaction with carbonyldiimidazole. 

Polymeric molecules contain reactive hydrogen sites in the form of alcohols and carboxylic acids. The reaction sequence, alcohol plus anhydride and acid plus oxirane, results in an increase of one in the degree of polymerization if the oxirane is DGEBA. Polymeric species also supply oxiranes via the pendant R. These reactions are generalized by the notation ... 

Synthesis of Acyl Nitronates The most general approach to the synthesis of acyl nitronates is based on the reactions of anions of the corresponding AN with acyl halides or carboxylic acid anhydrides in the presence of bases. Here, we will not consider a series of studies, where the formation of intermediate O-acyl nitronates was postulated without conclusive proof or by detection of their decomposition products. 

Carboxylic acids were introduced by the reaction of the polysilane(II) with carboxylic acid anhydrides in the presence of an amine. Table 2 shows the results. In order to examine the effect of unsaturated bonds and halides in the side chain on photolysis, double bonds or chloride groups were introduced with the carboxylic acid. Polysilanes(III) were also soluble in polar solvents and basic aqueous solution. The solubility in tetramethyl ammonium hydroxide aqueous solution(TMAH) depended strongly... 

Hill, C.A.S. and Hillier, J. (1999). Kinetic studies of the reaction of carboxylic acid anhydrides with wood. Experimental determination and modelling of kinetic profiles. Physical Chemistry and Chemical Physics, 1, 1569-1576. 

Hill, C.A.S. and Jones, D. (1996a). The dimensional stabilisation of Corsican pine sapwood by reaction with carboxylic acid anhydrides. Holrforschung, 50(5), 457 62. 

An electrochemical explanation of the basic reaction was suggested by P rumkin 17), while Shilov et al. 22, 23) claimed surface oxides of definite structure to be the only cause of either acidic or basic reaction. Shilov formulated the acidic surface oxides as carboxylic acid anhydrides bound to the edges of the carbon layers. 

Carboxylalkyltellurium trichlorides, obtained by the reaction of tellurium tetrachloride with carboxylic acid anhydrides, are reduced to the corresponding ditellurides with potassium hydrogen sulphite. - ... 

The classes of compounds which are conveniently considered together as derivatives of carboxylic acids include the carboxylic acid anhydrides, acyl chlorides, esters, and amides. In the case of simple aliphatic and aromatic acids, synthetic transformations among these derivatives are usually a straightforward matter involving such fundamental reactions as ester saponification, formation of acyl chlorides, and the reactions of amines with acid anhydrides or acyl chlorides ... 

---