Fumaric acid, diethyl ester

Diethyl fumarate Fumaric acid, diethyl ester (8) 2-Butenedioic acid ( )-, diethyl ester (9) (623-91-6)... 

Beilstein Handbook Reference) AI3-05613 Anti-Psoriaticum BRN 0775347 2-Butenedioic acid (E)-, diethyl ester 2-Butenedioic acid (2E)-, diethyl ester 2-Butenedioic acid, diethyl ester, (E)- trans-2-Butenedioic acid diethyl ester Diethyl fumarate Diethylester kyseliny fumarove EINECS 210-819-7 Fumaric acid, diethyl ester HSDB 5722 NSC 20954. Uquid mp = 0.8" bp = 214° d = 1.0452 Am" 213 nm (MeOH) insoluble in H2O, soluble in Me2CO, CHCI3. 

C2H2(COOC2Hs)2 (tram), fumaric acid, diethyl ester CH CH2 CHa... 

C8H11CIO4 chloro-fumaric acid diethyl ester 10302-94-0... 

Butenedioic acid, diethyl ester, (E)-. See Dimethyl fumarate... 

Elving and co-workers [39, 40] investigated the polarographic behavior of mono- anddibromosubstituted maleic andfumaric acids and their esters. Monobromomaleic acid is reduced to maleic, fumaric, and butadiene-1,2,3,4-tetracarboxylic acid, where the proportions of the products depend on the pH value. Monobromofumaric acid is reduced to fumaric acid. The esters of both acids are reduced to the esters of unsubstituted fumaric acid. Dibromomaleic and dibromofumaric acids and their esters are reduced to acetylene-dicarboxylic acid, and the half-wave potentials of the cis acid and its diethyl ester are less negative (by 0.04-0.18 and 0.10-0.12 V, respectively, depending on the pH value) than the half-wave potentials of the trans compounds. 

A-Phenylthiomethylpipecolic acid methyl ester afforded with methyl cin-namate and a mixture of two regioisomers 65 and 66 (84TL1579). Pipecolic acid and diethyl fumarate or maleinate gave three isomers (85TL2775). 

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... 

When iwo parts of (3) and one part of (I) are heated with copper at 75°, the product is the pure trans,lrans-ester (2). When (1) or (3) is heated separately with copper and hcnzoic acid, the major product is diethyl fumarate or diethyl maleate, respectively. These diesteis are probably formed by protonolysis of an organocopper intermediate, with complete retention of configuration. 

Condensations of chloroacetyl chloride (and similar compounds) with substituted ethylenediamines to give 1,4-disubstituted piperazin-2-ones have been described, and a number of 4-alkyl(or aralkyl)- -arylpiperazin-2-ones has been prepared either by catalytic debenzylation or pyrolytic debenzylation (or demethylation) of I,l-dialkyl(or l,l-diaralkyl)-3-oxo-4-arylpiperazinium halides (1609). 3-Ethoxy-carbonylmethylene-6-methylpiperazin-2-one has been synthesized by the reaction of diethyl acetylenedicarboxylate with propylenediamine (1610), and treatment of diethyl fumarate with propylenediamine has been shown to give 3-ethoxycarbonyl-methyl-6-methylpiperazin-2-one, also prepared from the diethyl ester of N- 2 -hydroxyiminopropyl)aspartic acid (84) (1611). 

Butenedioic acid (E)-, diethyl ester diethyl fumarate 404 ... 

Malathion, pH 4 Malathion pH 8 Malathion elimination Malathion ester 4.8 X 10 5.5 3.9 1.4 4.8 X 10 5.5 X 10 4.5 year 35 h Mono-acids Diethyl and ethyl hydrogen fumarates, dimethylphos-phorodiothioic acid Mono acid... 

Occasionally, a contaminant in unsaturated polyester resins due to the reaction between free fumaric acid and ethanol. Sometimes occurs as contaminant in the insecticide Malathion Synonyms ethyl fumarate 2-butenedioic acid (E) diethyl ester... 

Addition of bromine has been the subject of a number of studies. When a neutral salt of maleic or fumaric acid (A = COO ) is brominated in water, the meso derivative is the predominant product. Bell and Pring also report that the meso product is obtained on bromination of the diethyl esters of fumaric and maleic acids. Terry and Eicheberger observed 78% meso product from disodium maleate, a cis addition product which is unexpected. The prevalent bromonium ion mechanism proposed by Roberts and Kim-ball could easily explain the trans addition as follows ... 

The conjugate addition of a carbanionic species across the activated double bond, such as in the esters of maleic and fumaric acid, are typical examples of Michael addition. Carbanions are usually generated using a base catalyst and, hence, reaction of MA itself has not been attempted. A representative example of the addition of diethyl malonate 74 to diethyl maleate, which produces the tetracarboxylic ester 75, is shown below. 

Poly(diethyl fumarate) 2698-06-6 2-Butenedioic acid (E>, diethyl ester, homopolymer R (C8H,204). 

Chromium (II) sulfate is capable of reducing a variety of functional groups under mild conditions 10). Of particular interest is its ability to reduce a,jS-unsaturated esters, acids, and nitriles to the corresponding saturated compounds. This capability is illustrated in the procedure by the reduction of diethyl fumarate. 

Chromium(II) sulfate is a versatile reagent for the mild reduction of a variety of bonds. Thus aqueous dimethylformamide solutions of this reagent at room temperature couple benzylic halides, reduce aliphatic monohalides to alkanes, convert vicinal dihalides to olefins, convert geminal halides to carben-oids, reduce acetylenes to /raw5-olefins, and reduce a,j3-unsatu-rated esters, acids, and nitriles to the corresponding saturated derivatives. These conditions also reduce aldehydes to alcohols. The reduction of diethyl fumarate described in this preparation illustrates the mildness of the reaction conditions for the reduction of acetylenes and o ,j8-unsaturated esters, acids, and nitriles. 

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