With anhydrides

Hydrogen peroxide undergoes two reactions with anhydride ... 

Isopropenyl acetate [108-22-5] which forms upon reaction of acetone [67-64-1] with anhydride, rearranges to acetylacetone [123-54-6] in the presence of BF3 (19) ... 

Rea.ctlons, As with other tertiary alcohols, esterification with carboxyUc acids is difficult and esters are prepared with anhydrides (181), acid chlorides (182), or ketene (183). Carbamic esters may be prepared by treatment with an isocyanate (184) or with phosgene followed by ammonia or an amine (185). 

The free maleic acid content in maleic anhydride is determined by direct potentiometric titration (166). The procedure involves the use of a tertiary amine, A/-ethylpipetidine [766-09-6J, as a titrant. A tertiary amine is chosen as a titrant since it is nonreactive with anhydrides (166,167). The titration is conducted in an anhydrous solvent system. Only one of the carboxyhc acid groups is titrated by this procedure. The second hydrogen s dissociation constant is too weak to titrate (166). This test method is not only used to determine the latent acid content in refined maleic acid, but also as a measure of the sample exposure to moisture during shipping. 

Diarylamines can be A/-alkylated with anhydrides and acyl haUdes or A/-alkylated with alkyl haUdes, alkyl sulfates, and tri- / -alkylphosphites. Diphenylamine derivatives of alkyl—aryl gaUium, germanium, phosphoms, and siUcon are known (17), eg, pentaphenylgermanamine [64653-46-9]. 

Propylene oxide can be copolymerized with other epoxides, such as ethylene oxide (qv) (25,29,30) or tetrahydrofiiran (31,32) to produce copolymer polyols. Copolymerization with anhydrides (33) or CO2 (34) results in polyesters and polycarbonates (qv), respectively. 

Ben zotricbl oride is hydrolyzed to benzoic acid by hot water, concentrated sulfuric acid, or dilute aqueous alkaH. Benzoyl chloride [98-88-4] is produced by the reaction of benzotrichloride with an equimolar amount of water or an equivalent of benzoic acid. The reaction is catalyzed by Lewis acids such as ferric chloride and zinc chloride (25). Reaction of benzotrichloride with other organic acids or with anhydrides yields mixtures of benzoyl chloride and the acid chloride derived from the acid or anhydride (26). Benzo triflu oride [98-08-8] is formed by the reaction of benzotrichloride with anhydrous hydrogen fluoride under both Hquid- and vapor-phase reaction conditions. 

The bisphenol A-derived epoxy resins are most frequendy cured with anhydrides, aUphatic amines, or polyamides, depending on desired end properties. Some of the outstanding properties are superior electrical properties, chemical resistance, heat resistance, and adhesion. Conventional epoxy resins range from low viscosity Hquids to soHd resins. 

Acylation of 2-methylpyrido[2,3-d]pyrimidines with anhydrides gives 2-acylmethyl derivatives (67), whilst bromination to the 7-bromomethyl derivative has been reported for 7-methylpyrido[3,2-d]pyrimidines (56JCS4433) in a synthesis of potential folic acid antagonists. 

Other A-hydroxyimides have been obtained by reaction of benzyloxyamine with anhydrides, a process used many years ago with hydroxylamine itself. 

As noted above, the steroid nucleus has been a favorite for the design for site directed alkylating antitumor drugs. Thus reaction of prednisolone (62) with anhydride 63 affords the 21 acylated derivative, prednimustine (64). ... 

For this use, the preferred powders are based on acrylic, epoxy or polyester and epoxy resins. For best colour, epoxy resins are crosslinked with anhydrides of dicarboxylic acids in the straight epoxy coatings, or with saturated polyesters of high acid content in the epoxy-polyester type. Acrylics contain epoxide rings via, for example, glycidyl methacrylate (CH2=C(CH3) —CO—O—CHj—CH —CH2), and these groups crosslink... 

Symmetrical anhydrides of unsubslituted monocarboxylic acids and cyclic anhydrides of dicarboxylic acids are named by replacing the word acid with anhydride. 

Marteau and G.H. Cady, The Reaction of Peroxydisulfuryl Difluoride with Anhydrides of Certain Perhalocarboxylic Acids to Form Per-haloacyl Fluorosulfates , Univ Wash, Seattle,... 

Sulfonic acids themselves are unfit for electrophilic transfer of sulfonyl groups because of the poor nucleofugality of the hydroxide anion. However, the high acidity obviously leads to an equilibrium between the acids and their anhydrides and water, from which water can be removed either by special reaction conditions (i.e., azeotropic distillation with appropriate solvents) or chemically with anhydride forming agents316 (equation 63). sulfonic acid anhydride sulfonylations are compiled in Table 10. 

Bourgeois et al. reported a new approach227 wherein poly(arylene ether sulfone) and poly(arylene ether ketone) were functionalized with anhydride and amine chain ends, respectively, to afford imide-linked copolymers. 

Reactions with anhydrides afford interesting compounds having a carboxylic acid function (Table 26, entries 5 and 7 and Figure 40). It is notable that in the case of succinic anhydride, if the reaction is carried out at 25 °C, only one substitution occurs on the nitrogen atom, if the temperature is increased to 180 °C, there is a second substitution giving rise to a heterocyclic substituent (Table 26, entries 5-8). 

For all the reactions with anhydrides it is preferable to use the free amine rather than the hydrochloride salt in order to reduce the amount of external base in the reaction mixture and thus obtain clean products. 

The condensation of aromatic aldehydes with anhydrides is called the Perkin reaction When the anhydride has two a hydrogens (as shown), dehydration always occurs the P-hydroxy acid salt is never isolated. In some cases, anhydrides of the form (R2CHC0)20 have been used, and then the hydroxy compound is the product since dehydration cannot take place. The base in the Perkin reaction is nearly always the salt of the acid corresponding to the anhydride. Although the Na and K salts have been most frequently used, higher yields and shorter reaction times have been reported for the Cs salt. Besides aromatic aldehydes, their vinylogs ArCH=CHCHO also give the reaction. Otherwise, the reaction is not suitable for aliphatic aldehydes. ... 

Note that these mechanisms are the reverse of those involved in the acid-catalyzed hydration of double bonds (15-3), in accord with the principle of microscopic reversibility. With anhydrides (e.g., P2O5, phthalic anhydride) as well as with some other reagents such as HMPA, it is likely that an ester is formed, and the leaving group is the conjugate base of the corresponding acid. In these cases, the mechanism can be El or E2. The mechanism with AI2O3 and other solid catalysts has been studied extensively but is poorly understood. 

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