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I. B. Rozentsveig Yu. A. Aizina K. A. Chernyshev L. V. Klyba E. R. Zhanchipova E. N. Sukhomazova L. B. Krivdin G. G. Levkovskaya 《Russian Journal of General Chemistry》2007,77(5):926-931
The mixtures of mono-and dihalothiophenesulfonyl chlorides, formed in the sulfochlorination reaction of 2,5-dichlorothiophene
and 2,5-dibromothiophene, were treated with aqueous ammonia and thus converted into mixtures of the corresponding stable thiophenesulfonamides.
The structure and composition of the latter were studied by physicochemical methods: GC-MS and 1H, 13C, 1H-13C HSQC, 1H-13C HMBC, and NOESY NMR spectroscopy. As a result of the above chemical transformations, 2,5-dichlorothiophene afforded a mixture
of 5-chlorothiophene-2-sulfonamide and 4,5-dichlorothiophene-3-sulfonamide in a roughly 70:30 ratio. In the case of 2,5-dibromothiophene,
a mixture of 5-bromothiophene-2-sulfonamide, 4,5-dibromothiophene-3-sulfonamide, and 3,5-dibromothiophene-2-sulfonamide (3:54:43)
was formed.
Original Russian Text I.B. Rozentsveig, Yu.A. Aizina, K.A. Chernyshev, L.V. Klyba, E.R. Zhanchipova, E.N. Sukhomazova, L.B.
Krivdin, G.G. Levkovskaya, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 5, pp. 831–836. 相似文献
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E. P. Levanova V. A. Grabel’nykh V. S. Vakhrina N. V. Russavskaya A. I. Albanov L. V. Klyba O. A. Tarasova I. B. Rozentsveig N. A. Korchevin 《Russian Journal of General Chemistry》2013,83(9):1660-1665
Dimethyldiselenide reacts with 2,3-dichloro-1-propene at 20–25°C in the hydrazine hydrate-KOH medium to form 2-chloro-3-methylselanyl-1-propene with 90% yield. Diphenyldiselenide in the reaction with 2,3-dichloro-1-propene, depending on the conditions, can give quite selectively four products: 2-chloro-3-phenylselanyl-1-propene, phenylselanylpropadiene, 1-phenylselanyl-1-propyne, and Z-1,2-bis(phenylselanyl)-1-propene. The effect of the selenium atom on the reaction direction and the products structure is discussed. 相似文献
4.
Nikonova V. S. Grabelnykh V. A. Bogdanova I. N. Sosnovskaya N. G. Istomina N. V. Russavskaya N. B. Rozentsveig I. B. Korchevin N. A. 《Russian Journal of General Chemistry》2021,91(5):814-819
Russian Journal of General Chemistry - A possibility of the synthesis of 1,4-dichalcogenins by the reaction of vinylidene chloride or 1,2-dichloroethene with elemental chalcogenes in a hydrazine... 相似文献
5.
Yu. A. Aizina I. B. Rozentsveig S. K. Petkevich V. I. Potkin G. G. Levkovskaya 《Russian Journal of Organic Chemistry》2014,50(3):355-360
The reaction of N,N-dichloro-2-methylbenzenesulfonamide with trichloroethylene gave a new representative of highly electrophilic N-sulfonyl polyhaloaldehyde imines, 2-methyl-N-(2,2,2-trichloroethylidene) benzenesulfonamide. High reactivity of the product was demonstrated in the addition of water and 2-methylbenzenesulfonamide and reactions with benzene, toluene, anisole, thiophene, and 2-chlorothiophene. N,N-Dichlorobenzenesulfonamides and N,N-dichlorotrifluoromethanesulfonamide failed to react with 1,1,3,3,4,4-hexachlorobut-1-ene and 1,1,2,3,4-pentachlorobuta-1,3-diene under the conditions ensuring formation of N-(2,2,2-trichloroethylidene)arenesulfonamides from N,N-dichloroarenesulfonamides and trichloroethylene. 相似文献
6.
E. P. Levanova V. A. Grabel’nykh V. S. Vakhrina N. V. Russavskaya A. I. Albanov I. B. Rozentsveig N. A. Korchevin 《Russian Journal of General Chemistry》2014,84(3):439-443
Dibenzyldisulfide and -diselenide react with 2,3-dichloro-1-propene in the system hydrazine hydrate-KOH by the domino mechanism: nucleophilic substitution of the allyl chlorine, dehydrochlorination with participation of the chlorine atom at the sp 2-carbon atom, allene-acetylene rearrangement, nucleophilic addition of the chalcogenide reagent to the triple bond. The effect of the nature of the chalcogen atom and the benzyl substituent on the studied domino reaction is discussed. 相似文献
7.
E. P. Levanova V. S. Vakhrina V. A. Grabel’nykh I. B. Rozentsveig N. V. Russavskaya A. I. Albanov L. V. Klyba N. A. Korchevin 《Russian Chemical Bulletin》2015,64(9):2083-2089
A reaction of organic dichalcogenides R2Y2 (R = Ph, Bn, Pr; Y = S, Se) with 1,4-dichlorobut-2-yne in the system hydrazine hydrate–KOH leads to four principal products: 1,4-bis(organylchalcogenyl)but-2-ynes, 1-organylchalcogenylbut-1-en-3-ynes, 4-organylchalcogenylbut-1-en-3-ynes, and 3(5)-methylpyrazole. The selectivity of the formation of individual products is determined by the ratio of the substrates used and the reaction temperature. A plausible mechanism of chalcogenation considered in the work agrees with the effect of the nature of chalcogene atoms and organic substituents R on stability of intermediates and products. The stabilization of carbanions by α chalcogene-containing groups corresponds to the following order: PhS > PhSe > BnS > BnSe > PrS. 相似文献
8.
G. N. Chernysheva I. V. Nikitin I. B. Rozentsveig 《Russian Journal of Organic Chemistry》2017,53(6):824-827
Reactions of N-(2,2,2-trichloroethyl)arenesulfonamides with primary alkyl bromides and iodides, allyl bromide, chloroacetonitrile, and benzyl chloride in acetonitrile on heating in the presence of potassium carbonate gave the corresponding N-alkyl-N-(2,2,2-trichloroethyl)arenesulfonamides. 相似文献
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G. N. Rozentsveig V. Yu. Serykh K. A. Chernyshev I. B. Rozentsveig G. G. Levkovskaya L. B. Krivdin 《Russian Journal of Organic Chemistry》2011,47(4):572-576
4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence
of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization
of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene.
The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide
fragment. 相似文献