Synthesis of (1H-pyrrol-2-ylsulfanyl)alkanoic acids

(1-Benzyl-1H-pyrrol-2-ylsulfanyl)acetic acid, 2- and 3-(1-benzyl-1H-pyrrol-2-ylsulfanyl)propionic acids, 1,1′-[1,4-phenylenebis(methylene)]bis[(1H-pyrrol-2-ylsulfanyl)acetic acid], and 1,1′-(hexane-1,6-diyl)bis-[(1H-pyrrol-2-ylsulfanyl)acetic acid] were synthesized for the first time by reactions of 1-benzyl-1H-pyrrole, 1,1′-[1,4-phenylenebis(methylene)]bis(1H-pyrrole), and 1,1′-(hexane-1,6-diyl)bis(1H-pyrrole) with thiourea, iodine, and the corresponding halogen-substituted alkanoic acids. 1-(4-Nitrophenyl)-1H-pyrrole failed to react with thiourea and iodine.     

Sulfur-containing carboxylic acids. Communication 3. Synthesis of β-(acetylthio)alkanoic acids amides

Conclusions Amides of -mercapto- or -(acetylthio)alkanoic acids were obtained by the reaction of -thiolactones or -(acetylthio)alkanoic acid chlorides with amines.For Communication 2, see [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 616–621, March, 1983.     

冠醚酮酸和烷酸的合成

本文介绍了在PPA存在下，由B15C5和DB18C6同过量的二羧酸发生酰化作用，得到酮酸1a～e和3a～c。再把所得相应的酮酸1a～e和3a～c利用黄鸣龙法制得4'-(ω－羧基多亚甲基)苯并-15-冠-5(2a～e)和4',4'(5')-二(ω-羧基多亚甲基)二苯并-18-冠-6(4a～c)等一系列ω-冠醚酮酸。     

Some fatty acids having an O-heterocycle in their terminal positions. II. ω-(3-Coumarinyl)alkanoic acids and ω-(2-chromonyl)alkanoic acids

Some ω-3-coumarinyl)alkanoic acids 1a , n = 3-6 were synthesized by cyclization of corresponding ethyl o-formylphenyl alkanedioate 3 with DBU followed by hydrolysis. By a similar cyclization, some ω-(2-chromonyl)alkanoic acids 2a , n = 3-6 were also obtained from the cyclization of corresponding o-acetylphenyl ethyl alkanedioate 4 .     

A free-radical reaction of alkanoic acids with tetrachloroethylene

The di-tert-butyl peroxide-initiated free-radical reaction of C₃-C₆ alkanoic acids with tetrachloroethylene results in the formation of a mixture of isomeric (trichlorovinyl)alkanoic acids with the predominant isomer bearing the trichlorovinyl group at the (–1) position.Translated fromIzveshya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 1011–1013, April, 1996.     

Aroylnitrile oxide cyclizations. 2. Synthesis of (3-aroylisoxazol-5-yl)alkanoic acids

Intermolecular cyclization of 1,3-dipolar aroylnitrile oxides to terminal alkynols followed by phase transfer catalyzed oxidation provided a short, convenient route to several novel (3-aroylisoxazol-5-yl)alkanoic acids.     

Lipase catalysed kinetic resolutions of 3-aryl alkanoic acids

Hydrolase catalysed kinetic resolutions leading to a series of 3-aryl alkanoic acids (?94% ee) are described. Hydrolysis of the ethyl esters with a series of hydrolases was undertaken to identify biocatalysts that yield the corresponding acids with excellent enantiopurity in each case. Steric and electronic effects on the efficiency and enantioselectivity of the biocatalytic transformation were also explored.     

Synthesis of some ω- (2,5-dichloro-3-thienyl)alkanoic acids and their intramolecular ring closure

The synthesis of 1-chloro-4,5,6,7-tetrahydrobenzo[c]-4-thiophenone and 1-chloro-5,6,7,8-tetrahydro-4H-cyclohepta[c]-4-thiophenone was accomplished by the cyclization of the acid chlorides of -(2,5-dichloro-3-thienyl)butyric acid and -(2,5-dichloro-3-thienyl)valeric acid, respectively, to 1,3-dichloro-4,5,6,7-tetrahydrobenzo[c]-4-thiophenone and 1,3-dichloro-5,6,7,8-tetrahydro-4H-cyclohepta[c]-4-thiophenone and by partial dehalogenation of the latter by heating with copper metal in propionic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1358–1360, October, 1971.     

Photochemical chlorination of alkanoic acids anchored to a polymeric support

The synthesis of 2-(poly-p-styryl)ethyl esters of hexanoic, heptanoic, octanoic, nonanoic and decanoic acids as well as (poly-p-styryl)methyl octanoate and poly-2-(nitro-p-styryl)ethyl octanoate are described and their photochlorination are studied and compared with the monomeric (conventional) photochlorination of the methyl, benzyl and 2-phenylethyl esters of these acids. Hypotheses are advanced to explain the results on monochlorination products.     

The Diels-Alder reactions of quinone imine ketals: a versatile synthesis of highly substituted 5-methoxyindoles

[reaction: see text]. N-benzoylated quinone imine ketals undergo smooth cycloadditions in a [4 + 2] sense to yield the expected cycloadducts. The crude cycloadducts, when subjected to a short series of simple transformations, produce synthetically useful quantities of 5-methoxyindoles in excellent overall yields.     

Some fatty acids having O-heterocycles in their terminal positions. III. ω-(2-Benzofuranyl)alkanoic acids

Some ω-(2-benzofuranyl)alkanoic acids 1 , n = 2-5 were synthesized by acylation of benzofuran with ω-(ethoxycarbonyl)alkanoic acids in trifluoroacetic anhydride followed by Wolff-Kishner reductions.     

Solubilities of normal alkanoic acids by the UNIFAC group contribution method

The UNIFAC group contribution method was applied to predict solubilities of C₁₀–C₂₂ normal alkanoic acids in hydrocarbons, esters, ketones, and alcohols. The results were compared with the literature experimental data. It was found that taking into account dimerization of the acids improves considerably the prediction accuracy.     

Some fatty acids having an O-heterocycle in their terminal positions. I. ω-(3-Chromonyl)alkanoic acids

Some ω-(3-chromonyl)alkanoic acid derivatives, 1a and 2a , n = 4, 5; 3a, 4a and 5a , n = 2-6, were synthesized by cyclization of corresponding methyl ω-(2-hydroxybenzoyl)alkanoates 7b or ethyl ω-(2,4-dihydroxybenzoyl)alkanoates 8b with N,N-dimethylformamide-dimethyl acetal or acetic anhydride-DBU followed by hydrolysis.     

Indole derivatives. 120. Synthesis of higher ω-(3-indolyl)alkanoic acids by alkylation of indole lactones

The alkylation of indole with the tridecanolide, pentadecanolide, and oxo lactones of ω-hydroxyethoxyundecanoic and ω-hydroxybutoxyundecanoic acids was investigated. Higher indolylalkanoic acids, viz., ω-(3-indolyl)undecanoic, ω-(3-indolyl)tride-canoic, and ω-(3-indolyl)pentadecanoic acids, were obtained. The scheme of the alkylation of indole with oxo lactones, and the difference in the rates of the reactions of the ester and lactone bonds, were established from the reaction products. See [1] for communication 119. Translated from Khimiya Getetotsiklicheskikh Soedinenii, No. 2, pp. 216–217, February, 1980.     

Indole derivatives CIII. Esterification of ω-(3-indolyl)alkanoic acids in the presence of sulfonate cation-exchange resins

Esters were obtained in satisfactory yields by reaction of-(3-indolyl)alkanoic acids with aliphatic alcohols of various structures in the presence of KU-2 and KU-36 sulfonate cation-exchange resins.See [1] for communication CII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1506–1508, November, 1974.     

A spin trap study of the one-step oxidative lactonization of alkanoic acids

Conclusions ESR spectroscopy and the spin trap method were used to show the intermediate formation of acyloxyl and 3-carboxyalkyl radicals in the direct oxidation of alkanoic acids to - lactones by the action of sodium peroxydisulfate.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2630–2633, November, 1986.     

High temperature kinetics of the thermal decomposition of the lower alkanoic acids

The thermal decomposition of propanoic acid dilute in argon has beenstudied in a single-pulse shock tube over the temperature range of 1100-1500 K and over the pressure range of 14-18 atm. The decomposition kinetics have been satisfactorily computer modelled by means of afree radical mechanism involving H and OH chains. Recent single-pulse shock tube product analyses of acetic acid decomposition have been computer modelled using a free radical mechanism for decarboxylation coupled to a unimolecular dehydration reaction. A comparison between the thermal decomposition kinetics of the C₁? C₃ alkanoic acids is made. The present studies do notprovide evidence for the participation of transition states involving a pentavalent carbon atom in the pyrolyses of the lower alkanoic acids.