Succinic anhydride derivatives

All lation. Maleic anhydride reacts with alkene and aromatic substrates having a C—H bond activated by a,P-unsaturation or an adjacent aromatic resonance (31,32) to produce the following succinic anhydride derivatives. 

Varshney et al. (3) prepared biocompatible and bioerodable poly(lactide-co-succinic anhydride) derivatives having a Young s modulus between about 1.5 and 3, which had enhanced surface degradation rates. 

Dicarbonylation in aprotic solvents yields acid anhydrides. Fulgide (dimethylene-succinic anhydride derivative) 78 was obtained in 49% yield by the Pd(0)-catalysed dicarbonylation of 2,5-dimethyl-3-hexyne-2,5-diol (76) via 77 in benzene [6], The fulgide-forming reaction proceeds more smoothyl using Pd(OAc)2 as the catalyst in the presence of iodine (Pd l2 = 1 1) instead of hydrochloric acid [18]. 

Acid-functionalized polybutadienes are most effective with fillers such as calcium carbonate and aluminum and magnesium hydroxides but are not as effective with silicas and other silicates. As with the succinic anhydride derivatives discussed above, it is assumed that the anhydride functional polymers react with the filler surface by... 

The structures of the adducts of ergosterol acetate and maleic anhydride, the first of which were isolated by Windaus and Lutringhaus in 1931, have been revised. 8 Qne is a normal adduct of endo configuration, in which the dienophile addition has occurred from the a-side. The others are produced by an addition at C-7 and concomitant abstraction of either the 9a or the 14a hydrogen to give the 7a-succinic anhydride derivatives of 3p-acetoxy-5,8,22-triene and 3p-acetoxyergosta-5,8 (14), 22-triene. Similar addition to the diene system with acrylonitrile and dimethyl diazodicarboxylate has been observed.85... 

A total synthesis of ( )-albene (138) includes an alternative method for converting a succinic anhydride derivative into a cyclopentenone. ... 

Chem. Descrip. Alkenyl succinic anhydride deriv. with an alkanolamide, nonionic coemulsifiers, conosion inhibitors, and lubricity additives Uses Emulsifier, conosion inhibitor, lubricant for metalworking fluids Features Biostable low foam exc. hard water stability Properties Dk. vise, free-flowing liq. clearly sol. in naphthenic oil sol. (turbid) in water acid no. 105-125 amine no. 140-168 pH 9-10 (1% in DMW)... 

Kozlowski et al. [18] obtained the p CD polymers, which were prepared by crosslinking of 3-CD with 2-(l-docosenyl)-succinic anhydride derivatives in anhydrous N,N-dimethylformamide in the presence of NaH. It was established that the elongation of the hydrocarbon chain in the obtained 3-CD polymer in the reaction with 2-(l-docosenyl)-succinic anhydride results in the selectivity for Pb(ll) ions in the ion transport with the use of this ion carrier. At room temperature the dimmer was obtained, while at 100°C the polymers of 34kD and 13.5 kD fractions were received. The transport kinetics investigation on dependence of the carrier and Pb(II) concentrations have shown that the transport by the dimmer proceeded by the facilitated mechanism, typical for liquid membranes. The polymer however, has shown a linear increase of the transport flux in dependence on metal concentration in the source phase, this fact indicating that the polymer form of 3-CD prefers probably the fixed site mechanism of transport. PIMs containing dimmer and polymer of CD, in the transport of Zn(II), Cu(II) and Pb(Il) showed selectivity orders Pb(Il) Cu(II), Zn([]), and Pb(II) Cu(II) > Zn(II), respectively. The high selectivity factor for Pb(II)/Cu(II) equal to 163 for the dimmer was achieved (Table 1). 

B) Acetic, succinic anhydride phthalic anhydride (and substituted derivatives). 

Friedel-Crafts acylation of 3,3-dimethyl-2-indolinone by succinic anhydride gives 3,3-dimethyl-5-(3-catboxyptopionyl)-2-indoline, which is used as an intermediate in the preparation of inotropic agents for treatment of heart failure (94). Antibacterial phlotophenone derivatives have been prepared by Friedel-Crafts acylation with ptopanoyl chlotide (95). 

Halogenation. Halogens add directly to the double bond of maleic anhydride to give dihalo succinic acids. However, different procedures are used for dihalomaleic anhydride derivatives. Fluorinated substrates offer access to difluoromaleic anhydride [669-78-3] (64). 

Isomerization. Maleic acid is isomerized to fumaric acid by thermal treatment and a variety of catalytic species. Isomerization occurs above the 130 to 140°C melting point range for maleic acid but below 230°C, at which point fumaric acid is dehydrated to maleic anhydride. Derivatives of maleic acid can also be isomerized. Kinetic data are available for both the uncatalyzed (73) and thiourea catalyzed (74) isomerizations of the cis to trans diacids. These data suggest that neither carbonium ion nor succinate intermediates are involved in the isomerization. Rather, conjugate addition imparts sufficient single bond character to afford rotation about the central C—C bond of the diacid (75). 

Reduction. Heterogeneous catalytic reduction processes provide effective routes for the production of maleic anhydride derivatives such as succinic anhydride [108-30-5] (26), succinates, y-butyrolactone [96-48-0] (27), tetrahydrofuran [109-99-9] (29), and 1,4-butanediol [110-63-4] (28). The technology for production of 1,4-butanediol from maleic anhydride has been reviewed (92,93). 

Lubrication oil additives represent another important market segment for maleic anhydride derivatives. The molecular stmctures of importance are adducts of polyalkenyl succinic anhydrides (see Lubrication and lubricants). These materials act as dispersants and corrosion inhibitors (see Dispersants Corrosion and corrosion control). One particularly important polyalkenyl succinic anhydride molecule in this market is polyisobutylene succinic anhydride (PIBSA) where the polyisobutylene group has a molecular weight of 900 to 1500. Other polyalkenes are also used. Polyalkenyl succinic anhydride is further derivatized with various amines to produce both dispersants and corrosion inhibitors. Another type of dispersant is a polyester produced from a polyalkenyl succinic anhydride and pentaerythritol [115-77-5]. 

Halogenation. Succinic acid and succinic anhydride react with halogens through the active methylene groups. Succinic acid heated in a closed vessel at 100°C with bromine yields 2,3-dibromosuccinic acid almost quantitatively. The yield is reduced in the presence of excess water as a result of the formation of brominated hydrocarbons. The anhydride gives the mono- or dibromo derivative, depending on the equivalents of bromine used. 

Friedel-Crafts Acylation. The Friedel-Crafts acylation procedure is the most important method for preparing aromatic ketones and thein derivatives. Acetyl chloride (acetic anhydride) reacts with benzene ia the presence of aluminum chloride or acid catalysts to produce acetophenone [98-86-2], CgHgO (1-phenylethanone). Benzene can also be condensed with dicarboxyHc acid anhydrides to yield benzoyl derivatives of carboxyHc acids. These benzoyl derivatives are often used for constmcting polycycHc molecules (Haworth reaction). For example, benzene reacts with succinic anhydride ia the presence of aluminum chloride to produce P-benzoylpropionic acid [2051-95-8] which is converted iato a-tetralone [529-34-0] (30). 

The diacids are characterized by two carboxyHc acid groups attached to a linear or branched hydrocarbon chain. AUphatic, linear dicarboxyhc acids of the general formula HOOC(CH2) COOH, and branched dicarboxyhc acids are the subject of this article. The more common aUphatic diacids (oxaUc, malonic, succinic, and adipic) as weU as the common unsaturated diacids (maleic acid, fumaric acid), the dimer acids (qv), and the aromatic diacids (phthaUc acids) are not discussed here (see Adipic acid Maleic anhydride, maleic acid, and fumaric acid Malonic acid and derivatives Oxalic acid Phthalic acid and OTHERBENZENE-POLYCARBOXYLIC ACIDS SucciNic ACID AND SUCCINIC ANHYDRIDE). The bihinctionahty of the diacids makes them versatile materials, ideally suited for a variety of condensation polymerization reactions. Several diacids are commercially important chemicals that are produced in multimillion kg quantities and find appHcation in a myriad of uses. 

With the saturated analogs, i.e. succinic anhydride and its derivatives, pyridazines are formed in only a few cases. The reaction has been applied to the preparation of perhydro-pyridazines and their 3,6-diones (68MI21200, 70JOC1468). For the synthesis of 4,5-dihalopyridazinones, /3-formylacrylic acids, for example mucochloric acid, are useful syn-thons (Scheme 80). 

Pd(Ph3P)4 and Bu3SnH convert the Alloc group to other amine derivatives when electrophiles such as (B0C)20, AcCl, TsCl, or succinic anhydride are added. Hydrolysis of the stannyl carbamate with acetic acid gives the free amine. 

Aroylation of 3-arylhydrazonoisatin with aroyl chlorides gave 1043, which cyclized with ammonium acetate to give [1,2,4]triazino[5,6-A>]indole 1044 (92MI1). Derivatives of 1045 were prepared (92MI1). Cyclocondensation of 5-ethyl-3-hydrazino-5/f[l,2,4]triazino[5,6-b]indole 165 with succinic anhydride in acetic acid gave pyridazinedione derivative 1046 (90MI7) (Scheme 197). 

A classical procedure for fusing a six-membered ring to an aromatic ring uses succinic anhydride or a derivative. An intermolecular acylation is followed by reduction and an intramolecular acylation. The reduction step is necessary to provide a more reactive ring for the second acylation. 

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