Succinic aldehyde

Na-Isopropylatropinium bromide (25) (ipratropium bromide) has been obtained11 by a Robinson-type total synthesis from succinic aldehyde, isopropylamine, and acetonedicarboxylic acid, followed by reduction of the carbonyl... 

Similarly succinic aldehyde (di-aldehyde) by treatment with ammonia yields pyrrole. 

Succin- aldehyde 3-Methyl- 1,6- hexanedial 3-Formyl 1, 6-hexanedial 4-Octene-l, 8-dial Alternating BD/Pr (%)... 

Some of these papers have to be water-resistant and pore free, which is why microcrystalline wax, cationic styrene-acrylic emulsions, alkenyl succinic aldehyde (ASA) plus cationic starch, and styrene-maleic-anhydride (SMA) are used. To achieve resistance to oil and fat mainly perfluorinated alkyl acids, carboximethyl-cellulose (CMC), alginates and stearyl-melamines are applied. 

In another simple and very useful method, the hemiacetal 190 is generated in a reductive metalorganic addition to succinic aldehyde and its hemiacetal. As the reaction works even in aqueous solution, both these compounds will be in equilibrium under these conditions [57]. 

When cinnamaldehyde, succinic acid and acetic anhydride are heated in the presence of litharge (PbO), the aldehyde and the succinic acid condense to give the dicarboxylic acid (I), which undergoes decarboxylation to give the pale yellow crystalline 1,8-diphenyloctatetrene (II), Kuhn has shown that as the... 

The condensation of aldehydes and ketones with succinic esters in the presence of sodium ethoxide is known as the Stobbe condensation. The reaction with sodium ethoxide is comparatively slow and a httlo reduction of the ketonic compound to the carbinol usually occurs a shorter reaction time and a better yield is generally obtained with the more powerful condensing agent potassium ieri.-butoxide or with sodium hydride. Thus benzophenone condenses with diethyl succinate in the presence of potassium [Pg.919]

Condensation with Aldehydes and Ketones. Succinic anhydride and succinic esters in the presence of different catalysts react in the gas phase with formaldehyde to give citraconic acid or anhydride and itaconic acid (94—96). Dialkyl acyl succinates are obtained by reaction of dialkyl succinates with C 4 aldehydes over peroxide catalysts (97). 

Succinic esters condense with aldehydes and ketones in the presence of bases, eg, sodium alkoxide or piperidine, to form monoesters of alkybdenesuccinic acids, eg, condensation of diethyl succinate with acetone yields ethyl 2-isopropyhdenesuccinate (eq. 3). This reaction, known as Stobbe condensation, is specific for succinic esters and substituted succinic esters (98,99). 

KNOEVENAGEL OOEBNER STOBBE Condensation Base catalyzed aldol condensation of aldehydes or ketones with an activated methylene group of a malonic ester (Knoevenagel Doebner) or a succinic ester (Stobbe)... 

BerL Ber., abbrev. (Berliner Berichte) Berickte der deutscken chemiachen Gesellscka/t. Berliner-blau, n. Berlin blue, Prussian blue, -blaus ure, /. hydrocyanic acid, -braun, n. Prussian brown, -griin, n. Prussian green, -rot, n. Berlin red (a red lake color), -saure,/. prussic acid, -weiss, n. a kind of white lead. Bernstein, m. amber. — schwarzer —, jet. Bernstein-, amber succinic, succinyl, succino-. -alaun, m. aluminous amber, -aldehyd, n. succinaldehyde. bemateinartig, a. amber-like. 

Aldehydes (glutaric, succinic [53-56]) are used to crosslink PVA, the network density being controlled by the ratio of aldehyde to OH-groups. The swelling degree of these hydrogels does not exceed 35-40 ml g-1, and there are almost quantitative correlations of the network density with the crosslinker concentration... 

Cyclobutane Butyrolactone Butyr aldehyde Succinic acid 1-Tetralone Carbonyls... 

In addition to these more-or-less well characterized proteins, iron is known to be bound to certain flavoproteins such as succinic dehydrogenase (20), aldehyde oxidase (27), xanthine oxidase (22) and dihydrooro-tate dehydrogenase (23). Iron is present and functional in non-heme segments of the electron transport chain but again no real structural information is at hand (24). 

L-dihydroxy-succinic acid (L(dexiro)-tartaric acid, CXIII). This result establishes the position of the double bond between C4 and C5 and demonstrates that C4 carries only one hydrogen atom while C5 has attached to it the enolic hydroxyl group. Treatment of the enol CXI with ethereal diazomethane gives 5-methyl-A4-D-glucosaccharo-3,6-lactone methyl ester (CXIY) which upon further methylation with silver oxide and methyl iodide yields 2,5-dimethyl-A4-D-glucosaccharo-3,6-lactone methyl ester (CXV). When the latter is subjected to ozonolysis there is formed oxalic acid and 3-methyl-L-threuronic acid (CXVI). Oxidation of this aldehydic acid (CXYI) with bromine gives rise to a monomethyl derivative (CXVII) of L-ilireo-dihydroxy-succinic acid. 

The first examples of a homogeneous reduction of this type were reported in 1971. Cobalt carbonyl was found to reduce anhydrides such as acetic anhydride, succinic anhydride and propionic anhydride to mixtures of aldehydes and acids. However, scant experimental details were recorded [94]. In 1975, Lyons reported that [Ru(PPh3)3Cl2] catalyzes the reduction of succinic and phthalic anhydrides to the lactones y-bulyrolaclone and phthalide, respectively [95], The proposed reaction sequence for phthalic anhydride is shown in Scheme 15.15. Conversion of phthalic anhydride was complete in 21 h at 90 °C, but yielded an equal mixture of the lactone, phthalide (TON = 100 TOF 5) and o-phthalic acid, which is presumably formed by hydrolysis of the anhydride by water during lactoniza-tion. Neither acid or lactone were further hydrogenated to any extent using this catalyst system, under these conditions. 

A mixture of 9.5 g pyrrolyl-2-aldehyde, 29.2 g dimethyl-succinate and NaH (9.6 g of 50% suspension in oil) in 100 ml benzene is stirred at room temperature 6 hours, cooled and carefully acidified with glacial acetic acid. Add water and ether and dry, evaporate in vacuum or work up (JACS 72,501 (1950), JCS 1025(1959)) to get ca. 17 g (80%) 3-methoxycarbonyl-4-(2 -pyrrolyl)-3-butenoic acid (I) (recrystallize-acetone-benzene). A mixture of 12 g (I), 7 g sodium acetate and 70 ml acetic anhydride is left overnight at room temperature with occasional shaking. Then gradually raise the temperature to 70-75° over 2 hours, maintain for 4 hours and work up (see JCS 1714(1955), 986( 1958)) to get ca. 8 g (60%) methyl-4-acetoxy-indole-6-carboxylate (II) (recrystallize-petroleum ether). If desired, this can be converted to 4-OH-indole-6-COOH and 4-methoxyindole-COOH as described in the ref. or decarboxylated as described elsewhere here. If the 1-methyl cpd. is used, 1-Me-indole results. 

Schaller M, Schaffhauser M, Sans N, et al. Cloning and expression of succinic semialdehyde reductase from human brain. Identity with aflatoxin B1 aldehyde reductase. Eur J Biochem 1999 265(3) 1056-1060. 

We initially prepared the first chitosan-sialoside hybrid 19 by treating 80% de-AT-acetylated chitosan with p-formylphenyl a-sialoside 6 (Scheme 1) under reductive amination conditions (NaBH3CN) (Scheme 7) [64]. The level of sialo-side incorporation could be controlled by increasing the amount of 6 (Table 15.2). The reactivity of aldehyde 6 toward chitosan was found to be in the range 25-48% due to excessive reduction of the aldehyde under the acidic reaction conditions. Water-soluble materials were only achieved at high DS (DS > 0.53). Sialo-hybrids with lower substitutions were further derivatized with succinic... 

Both CH2-groups of succinic acid are capable of taking part in condensations. If unsaturated aldehydes such as cinnamaldehyde are... 

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