Dioic acids

The reaction usually proceeds with explosive violence and a better method of preparation is to heat, gently, moist crystals of ethane-dioic acid (oxalic acid) and potassium chlorate(V) ... 

Compounds with two carboxyl groups as illustrated by entries 10 through 12 are distinguished by the suffix dioic acid or dicarboxylic acid as appropnafe The final e m fhe base name of fhe alkane is refamed... 

Butane, 2,3-0-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)-catalyst in homogeneous asymmetric hydrogenation, 6, 781 Butane-1,4-dioic acid, 2,2-di(indolyl)-synthesis, 4, 226 Butanenitrile, 4-hydroxy-dihydropyran synthesis from, 3, 769 Butanoic acid, -y-aryl-y-amino-synthesis, 1, 433 1-Butanol... 

Diglycolic acid (2-oxapentane-l,5-dioic acid) [110-99-6] M 134.1, m 148 (monohydrate), pKj 2.97, pKj 4.37. Crystd from water. 

Dodecane-l,10-dioic acid (decane-1,10-dicarboxylic acid) [693-23-2] M 230.3, m 129°, b 245°/10mm, pK ,t -4.8. Crystd from water, 75% or 95% EtOH (sol 10%), or glacial acetic acid. 

Pimelic acid (heptane-1,7-dioic acid) [111-16-0] M 160.2, m 105-106 , pK 4.46, 5.58. Crystd from water or from benzene containing 5% diethyl ether. 

The position of the keto group of A-homo-5a-cholestan-3-one (5b) was determined by Nelson and Schut by an unambiguous synthesis of ketone (5b) involving bis-homologation of 2,3-seco-5a-cholestane-2,3-dioic acid (8) using the Arndt-Eistert sequence [(9) (11)]. 

Acetoxy-A-nor-5a-androstan-2-one (3) l7 -Acetoxy-2,3-seco-5a-An-drostane-2,3-dioic Acid (2). This an an adaptation of the method of Riill and Ourission. ... 

Acetoxypregna-5,16-dien-20-one, 211 3/3-Acetoxy-5a-pregnane-l 1,20-dione, 207 3 a-Acetoxy-5/3-pregnane-20-one, 178 3/3-Acetoxypregn-5-en-20-one, 71 3 /3-Acetoxypregn-5-en-20-one-[l 7 a, 16a-c]-A -pyrazoline, 106 3/3-Acetoxy-5a-pregn-9( 1 l)-en-20-one-[17a, 16a-c]-Ai-pyr azoline, 106, 107 17/3-Acetoxy-2,3-seco-5a-androstan-2,3-dioic acid, 409... 

Schmidt rearrangement, 144 2,3-Seco-cholestane-2,3-dioic acid, 356... 

Compounds with two car boxyl groups, as illustrated by entries 10 through 12, are distinguished by the suffix -dioic acid or -dicarboxylic acid as appropriate. The final -e in the base nane of the alkane is retained. 

One after the other, examine structures for octane-1,8-dioic acid, nonane-1,9-dioic acid djud decane-1,10-dioic acid. Is there any difference (in structure or conformation) between the diacids with lower and higher melting points Which, if any, of the acids adopt structures similar to that of acetic acid dimer Account for the variation in melting points of these three compounds. 

Cyclododecatriene is a precursor for dodecane-dioic acid through a hydrogenation step followed hy oxidation. The diacid is a monomer for the production of nylon 6/12. 

Considerable interest arose during the 1970 s and 1980 s in the use of micro-organisms to produce useful fatty adds and related compounds from hydrocarbons derived from the petroleum industry. During this period, a large number of patents were granted in Europe, USA and Japan protecting processes leading to the production of alkanols, alkyl oxides, ketones, alkanoic adds, alkane dioic acids and surfactants from hydrocarbons. Many of these processes involved the use of bacteria and yeasts associated with hydrocarbon catabolism. 

Cx-dioic acid Cx (x can be between 10-22) Wide range of organisms including Candda sp, Torulopsis sp, Corynebacterium sp. 

This cyclization reaction has been used in the synthesis of a number of A -substituted 5-hy-droxy-2-pyrrolidinones by Lemieux Johnson oxidation of the corresponding amides of the ( )- or (i5)-4-octene-l,8-dioic acids according to the procedure described. 

Oxamide (Oxalamide, Oxalic acid diamide, Ethane diamide, Ethane dioic acid diamide). H2N.CO.CO.NH2, mw 88.07, N 31.81%, OB to C02 -72.67% white, odorl powd, triclinic needles mp 417—19° decomp, d 1.667g/cc, sparingly sol in hot w, ale, insol in eth (Refs 1,... 

C,4Hi C1FN02) see Sertindole [[(3-chloro-4-fluorophenyl)amino]methylene]propane-dioic acid diethyl ester... 

C21H22F3N3OS 807-57-8) see Fluphenazine Y-[4-(trifluoromethyl)phenoxyJbenzenepropanamine -(Ci HiftFjNO 83891-03-6) see Fluoxetine (3-trifluoromethylphenyl)acetone (CioHgFjO 21906-39-8) see Fenfluramine (3-trifluoromethylphenyl)acetone oxime (CiijHkjFjNO, 834-19-5) see Fenfluramine [[[2-(trifiuoromethyl)phenyl]amino]methylene]propane-dioic acid diethyl ester (C 3Hi(,F3N04 23779-94-4) see Floctafenine... 

It is not normally possible to add fluorine directly to alkenes as the reaction is so exothermic that bond fission occurs. Many alkenes will not add iodine directly either, and when the reaction does occur it is usually readily reversible. Alkynes are also found to undergo preferential, though not exclusive, ANTI addition of halogens, e.g. with butyne-l,2-dioic acid (17) ... 

Polar-substituted alkenes where the functionality is not attached to a strained ring are considerably more discriminating in their compatibility with metathesis catalysts and as a rule require relatively high catalyst charges. In the aliphatic series, unsaturated esters have received the most attention. Boelhouwer reported in 1972 the metathesis of the ester methyl oleate and its trans isomer, methyl elaidate, with a homogeneous catalyst based on a 1/1.4 molar combination of WCl6/(CH3)4Sn (23). At 70°C and an ester/W molar ratio of 33, near-thermodynamic equilibrium was attained, and 49 and 52% of the respective esters were converted to equal amounts of 9-octadecene and the dimethyl ester of 9-octadecene-1,18-dioic acid. 

These reactions, which are believed to occur predominantly inter-molecularly, are capable of producing intermediates which hold some potential as precursors for important chemical products. For example, metathesis of olive oil, which consists chiefly of triglycerides of oleic acid, produces the glyceride of 9-octadecene-l,l8-dioic acid from which can be obtained, after saponification, acidification, and low-temperature crystallization, the free acid, which can be transformed by intramolecular condensation to civetone. 

The first example of a heterogeneous catalyst able to metathesize olefinic esters was recently reported (92). The combination of Re207/ (CH3)4Sn at an olefin/Re/Sn molar ratio of 219/6/1 converted methyl 4-pentenoate at 50°C in 51% conversion to ethylene and the corresponding dimethyl ester of 4-octene-l,8-dioic acid. This reaction exhibited a high degree of selectivity (>99%), and in the absence of (CH3)4Sn the rhenium catalyst was inactive (90). 

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