Butane-1,1-dicarboxylic acid

Using hydroformylation and other catalytic or stoichiometric reactions, how could the following transformations be achieved in one or more steps (a) Ethylene to 2-methylpentanol (b) butadiene to 1,6-hexanediol (c) allyl alcohol to butane 1,4-dicarboxylic acid (d) allyl alcohol to 4-carboxylic butanal. 

Succinic anhydride The cyclic anhydride of butane-1,4-dicarboxylic acid. 

Amjad and McAuley (1974) have investigated the oxidation of malic (2-hydroxy-butane-1,4-dicarboxylic) acid in perchloric add. The reaction occurs at stopped-flow lifetimes and is unaffected by either Ce(III) or nitrate. The Michaelis-Menten plot is linear with finite positive intercept indicating precursor complex formation. The resolved values for the formation constants are comparable to those reported for the hydroxy and keto monocarboxylates, suggesting that the second carboxylate group is not bound in the activated complex. The intramolecular electron transfer rate parameters are less than those reported by Hanna and Fenton for the cyclic a-hydroxycarboxylic acids. 

ADIPIC ACID Adipinic Acid, 1,4 -Butane-dicarboxylic Acid, Hexanedioic Acid 1 1 0 ... 

Adipic acid (1,6-hexane-dioic acid,l,4-butane-dicarboxylic acid) [124-04-9]... 

A substituted acetamidomalonic ester, tetraethyl 1 -acetamido-4-hydroxy-butane-l,l,3,3-tetracarboxylate, was used in the preparation of cis- and frans-pyrrolidine-2,4-dicarboxylic acids, cyclic analogs of glutamic acid (91TL3049). 

Commercially important polyesters, e.g. poly[l-(2-ethylenyl)-2,2,6,6-tetramethyl-4-piperidinylbutane dioate] (146) [190] were synthesized from l-(2-hydroxyethyl)-4-hydroxy-2,2,6,6-tetramethylpiperidines and suitable dicarboxylic acids. Another polymeric HALS was prepared by transesterification of oligoesters of tetramethyl-butane-l,2,3,4-tetracarboxylate with 22,6,6-tetramethyl-4-hydroxypiperidine and 1,10-decanediol [191]. Compound 147 is a similar polyester type HALS. An ester-amide chain is created during esterification of 2-(2,2,6,6-tetramethyl-4-piperidinylamino)ethanol and dimethyl adipate [192]. 

Draw the three-dimensional structures of the following, indicating the interactions that may exist (a) -butane in its staggered form (b) -butane in its eclipsed form about the 2,3-bond (c) 1,2-dibromoethane in its most stable form (d) cyclopropane (e) 1,2-epoxyethane (ethylene oxide) showing the lone pairs of electrons on the oxygen (f) cis- and rart.v-1,4-dimethylcyclohexane in the chair form (g) /ran.v-cyclohexane-l,2-dicarboxylic acid (h) cyclohexene. 

A series of salts derived from alpha omega diamines, namely 1,3-propane- and 1,4-butane diamine, and various dicarboxylic acids was studied with the aim of extending ID PAD to 2D DPAD synthon. SXRD studies on 9 salts out of the 14 prepared revealed that none of the salts displayed the expected 2D DPAD synthon instead, 3D HBN was observed in these salts and consequently, only 2 salts were able to gel a few solvents [98]. 

The inactive ethyl ester is a colorless oil, = 1.4681. Iodine number C20H34O2, calculated 248 found 216/217 (28 ). Melting point of hydrogenated acid 68.0-68.5°. Results of oxidative and reductive ozonolysis dicarboxylic acids (Cio 0.95 C3 0.88 mole/mole FA) DNPH of butanal (0.63 mole/mole FA). 

Won et al. [19], have reported synthesis of polyesters with valine, leucine, isoleucine, methionine, and phenylalanine (Table 12.1). This three-step process involves synthesis of a diester and a dinitro compound that are copolymerized [19], An amino acid is first coupled with a diol (with 3, 4, or 6 methylene groups) in the presence of tosyl to yield a diester with acid salts of diamine at the terminal ends. The second monomer, di-p-nitrophenyl ester of carboxylic acids, is synthesized by a condensation reaction of adipoyl or se-bacoyl chloride with p-nitro phenol. The final polymerization step involves an arduous condensation reaction in the presence of a strong proton abstractor between acid salt of bis(amino acid-alkyne diester) and di-p-nitrophenyl ester of dicarboxylic acids. Following along the same lines, Chu and Guo [22] have copolymerized a mixture of nitro phenyl ester of succinate, adipate, or sebacate and nitrophenyl fumarate with toluenesulfonic acid salt of phenylalanine butane-1,4-diester. The addition of fumarate derivative to the monomer mixture provides an unsaturated double bond in the polymer backbone that can be functionalized for specific biomedical... 

As far back as 1894 an attempt was made to prepare cyclobutadiene--1,2-dicarboxylic acid, by the action of alkali on 1,2-dib romocyclo-butane-l,2-dicaTboxylIc acid only cyclobutene derivatives were obtained [2]. 

Moore JM, Allen AC, Cooper DA (1984) Determination of manufacturing impurities in heroin by capillary gas chromatography with electron capture detection after deri-vatization with heptafluorobutyric anhydride. Anal Chem 56 642-646 Moore JM, Cooper DA, Lurie IS, Kram TC, Carr S, Harper C, Yeh J (1987) Capillary gas chromatographic-electron capture detection of coca-leaf-related impurities in illicit cocaine 2,4-diphenylcyclobutane-l,3-dicarboxylic acids, 1,4-diphenylcyclo-butane-2,3-dicarboxylic acids and their alkaloidal precursors, the truxillines. J Chromatogr 410 297-318... 

We, thus, initiated a study involving co-crystallizations of simple dicarboxylic acids and p-PTE. In particular, co-crystallization of p-PTE and succinic acid (SA) resulted in a three-component linear assembly sustained by the COOH- N heterosynthon (Fig. 4a). The assemblies stacked in offset layers to afford a head-to-tail arrangement of p-PTE, which were separated on the order of 3.99 A and packed as pairs surrounded by SA molecules (Fig. 4b). Upon UV-irradiation, conversion to the head-to-tail cyclobutane rctM,3-bis(4-pyridyl)-2,4-bis(3-thienyl)cyclo-butane (4p3tc) was achieved regiospecifically and in quantitative yield (Fig. 4c). ... 

Methyl acrylate [30,31], methyl methacrylate and acrylonitrile [31,33] can be dicarboxylated with yields up to 60 %. The electrocarboxyla-tive dimerization of methyl acrylate leads to 1,1,4,4-tetracarboxy-butane. Dicarboxylation of stilbenes yields 2,3-diphenylsuccinic acid [33,34]. Styrene can be carboxylated to 2-phenylsuccinic acid or to 3-phenylpropionic acid [35] and ethene reacts to succinic acid [36]... 

A reaction related to cleavage is aromatic ring degradation. Phthalic anhydride used to be prepared from naphthalene, and maleic anhydride from benzene, with air and V2O5 catalyst, losing 2 carbon atoms as CO2. More modern processes use o-xylene and butadiene (or -butane) respectively. However, the analogous formation of quinolinic (pyridine-2,3-dicarboxylic) acid from quinoline is still practised. Hypochlorite [94], hypochlorite or chlorite/Ru catalyst [95], or simply alkaline H2O2 [96] can be used. 

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