Dicarboxylic acid imides amides

Sodium hydride C-Acylation with diacylamines Ketocarboxylic acid amides from dicarboxylic acid imides... 

Lactams from dicarboxylic acid amide esters via dicarboxylic acid imides by decarbonylation... 

N-Aminodicarboxylic acid imides from dicarboxylic acid imides via dicarboxylic acid amide hydrazides... 

Cobalt carbonyl Dicarboxylic acid imides from ethylenecarboxylic acid amides s. 19, 777... 

Dicarboxylic acid imides e.g. (189) were prepared in high yield by cyclization of carboxylic acid amides (190) with trifluoroacetic acid this technique avoided dehydration to the nitrile (191), which was easily achieved with acetic anhydride. This work is part of a total synthesis of maleimycin. ... 

Dicarboxylic acid imides from dicarboxylic acid amide esters Dicarboxylic acid monothioimides from dicarboxylic acid thiamide esters... 

R) - and (S)-l-phenylethylamine to the diethyl esters of fumaric and maleic acid which are carried out by heating the pure compounds, without solvent, to 115-120 °C for three days (see Table 1). The reaction mixtures are then hydrolyzed and hydrogenated to give aspartic acids in high yields (85-87%) but very low optical purities (6.3-12.2%). A number of intermediates and by-products arc isolated, especially amides and imides of the dicarboxylic acids participating in the reaction. This may explain the low overall diastereoselectivity which can be calculated from the low optical rotation of the isolated aspartic acids. However, any discussion of the reaction mechanism remains difficult because the structures of the substrates and products of the actual addition step itself are not known with certainty. It is known that... 

Kricheldorf has reported the synthesis of lyotropic poly(amide-imide)s and poly(benzoxazole-amide)s. These were prepared by the polycondensation of N,N-bis(trimethylsilyl)-p-phenylenediamine or N,AT -bis(trimethylsilyl)-3,3 -dim-ethylbenzidine with the diacyl chloride of trimellitimide of p-aminobenzoic acid, or the imide formed from p-amino benzoic acid and terephthalic acid. Lyotropic behaviour was observed in cone, sulphuric acid solution [38]. A series of thermotropic poly(imide-amide)s was prepared based on trimellitimides formed from trimellitic anhydride and an a, -bis(4-aminophenoxy) alkane with carbon chain lengths 9-12. Melting points were in the range 250-300 °C. They formed smectic A phases and tended to degrade around the isotropisation temperatures (around 350 °C). Pendant methyl groups or occupied meta- groups tended to prevent mesophase formation [39]. Novel LC poly(imide-amides) have also been synthesised from new diamine spacers derived from linear diaminoalkanes and 4-nitrophthalic anhydride. A smectic and nematic phase were observed when 4,4 -biphenyl dicarboxylic acid was used as co-monomer [40]. 

PAIs can be prepared by the condensation of a monoanhydride of a tricarboxylic acid and a primary diamine. Further PAI can be prepared by tbe reaction of dicarboxylic acid chlorides and diamines. Here, either the diamines or diacid halides already contain imide linkages, or mutatis mutandis, amide linkages. Classical PAI are usually obtained by reacting equimolar amounts of trimellitic acid hahde anhydride and a diamine. ... 

Abouzari-Lotf E, Shockravi A, Javadi A. Heat-resistant and soluble fluorinated poly(amide imide)s based on non-coplanar ortho-linked diimide-dicarboxylic acid. Polym Degradation Stability 2011 96(5) 1022-8. 

Dicarboxylic acid amide hydrazides from imides s. 44, 383 G... 

C.P. Yang, YY Su, M.Y. Hsu, Syntheses and properties of fluorinated polyamides and poly(amide imide)s based on 9,9-bis [4-(4-amino-2-rifluromethylphenoxy) phenyl] fluroene, aromatic dicarboxylic acids, and various mono-trimellitimides and te-trimellitimides. Colloid Polym. Sci. 284 (9) (2006) 990-1000. 

There are cyclic esters (known as lactones), cyclic amides (known as lactams), cyclic anhydrides, and cyclic imides. The structures for these derivatives are presented in Chapter 20, Section 20.6.5. The chemical reactions associated with derivatives of dicarboxylic acids are discussed in Chapter 20 as well. 

Imides are formed by the reaction of amides with other acid derivatives. Cyclic anhydrides and cyclic imides can be prepared from dicarboxylic acids or acid dichlorides. 

Virtually any of the traditional methods outlined to prepare polyamides, particularly aromatic polyimides, has readily been used for the synthesis of poly(amide imide)s from diamines or diamine derivatives and imide-containing dicarboxylic acids or acid derivatives (Scheme 35). 

S.E. Mallakpour, A.R. Hajipour, S. Khoee, optically active poly(amide-imide)s by direct polycondensation of aromatic dicarboxylic acid with aromatic diamines. Europ. Poly. J. 38, 2011-2016 (2002)... 

The separation of gas mixtures by polymeric membranes has become a commercially important methodology for a number of different systems (1). Several recent review articles have discussed the interaction between polymer structure and gas permeability properties (2,3). The quantification of the effect of polymer structure on gas transport properties recently has been reported (4,5) and it is now possible to optimize gas transport properties for well defined polymeric materials. For those materials which do not have a well defined data base it is necessary to prepare and measure the gas transport properties. The polyamide-imides (PAI) are a class of polymeric materials which do not have an extensive data base for gas transport properties (6,7). Work by Yamazaki and coworkers (8) demonstrated that PAI materials could be prepared easily and in a manner whereby the amide bond could be prepared from a phosphite activated carboxylic acid and an aromatic amine. Yang and CO workers (9-11) have shown that novel dicarboxyl ic acids could be prepared from trimellitic acid anhydride (TMA) and aromatic diamines and that these dicarboxylic acids could be coupled with a second diamine to form regiospecific PAI materials. Our focus was to examine the effects of a phenylene diamine and its alkylated analogs on the gas transport properties of regiospecific PAI materials and to identify those structures which maximized both permeability and selectivity. 

A perfect transformation of an a2 + b2b into an ab2 polycondensation was first reported by a team of DSM NV [78, 79], Bis(2hydroxypropyl)amine reacts rapidly and almost quantitatively with the amino group, so that a bis(hydroxyalkyl) carboxylic acid is formed (see Formula 10.5). The polyesterification at higher temperatures yields a poly(ester amide), which was commercialized under the trademark Hybrane. Another example of an in situ formation of an ab2 monomer was described by Shu et al. [80]. The reaction of 1,4-diaminobenzene with the monoanhydride of a diphenyl ether tetracarboxylic acid (see Formula 10.5) produces an amino dicarboxylic acid which upon further polycondensation yields a hb poly(amide imide). Polycondensations of 4,3, 5 -trifluorodiphenylsulfone with commercial diphenols were studied by the Fossum group [81, 82]. The para C-F bond id particular reactive and substitution of one meta-position lowers the reactivity of the last C-F group. Therefore, variation of the reactions conditions allows for systematic variation of the DB. 

An acid—base reaction forms a nucleophilic anion that can react with an unhindered alkyl halide— that is, CH3X or RCH2X—in an 5 2 reaction to form a substitution product. This alkylated imide is then hydrolyzed with aqueous base to give a 1° amine and a dicarboxylate. This reaction is similar to the hydrolysis of amides to afford carboxylate anions and amines, as discussed in Section 22.13. The overall result of this two-step sequence is nucleophilic substitution of X by NH2, so the Gabriel synthesis can be used to prepare 1° amines only. 

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