40973-72-6Relevant academic research and scientific papers
Nucleophilic Cleavage of the Ether Bond of Chlorex in the Chalcogenation with Diphenyl Dichalcogenides in the System Hydrazine Hydrate–KOH
Albanov, A. I.,Bogdanova, I. N.,Grabel?nykh, V. A.,Istomina, N. V.,Korchevin, N. A.,Nikonova, V. S.,Rozentsveig, I. B.,Russavskaya, N. V.,Sosnovskaya, N. G.
, p. 1760 - 1762 (2020/10/15)
Abstract: The synthesis of unsymmetrical pincer ligands by reactions of diphenyl disulfide and diphenyl diselenide with bis(2-chloroethyl) ether in the system hydrazine hydrate–KOH was accompanied by the formation of 1,2-bis(phenylsulfanyl)ethane, 1,2-bis(phenylselanyl)ethane, and 1-(phenylselanyl)-2-(phenylsulfanyl)ethane as by-products with an overall yield of 23% as a result of nucleophilic cleavage of the C–O–C bond in the initial ether.
Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies
Trofymchuk, Oleksandra S.,Zheng, Zhipeng,Kurogi, Takashi,Mindiola, Daniel J.,Walsh, Patrick J.
supporting information, p. 1685 - 1692 (2018/03/21)
A new organocatalyst, the selenolate anion [RSe]–, generated from bench-stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10 mol%) is introduced. Benchmarking is performed in the conversion of benzylic chlorides into trans-stilbenes selectively at room temperature. Mechanistic studies support the intermediacy of the selenolate anion and of 1,2-diphenylethyl phenyl selenide. (Figure presented.).
Chalcogenation of 1,3-Dichlorobut-2-ene with Organic Dichalcogenides in the System Hydrazine Hydrate–Alkali
Levanova,Nikonova,Grabel’nykh,Russavskaya,Chirkina,Albanov,Rozentsveig,Korchevin
, p. 1754 - 1759 (2019/03/26)
Electron-donor effect of the methyl group in 1,3-dichlorobut-2-ene hampers allylic rearrangement of its primary monochalcogenation products. The use of diphenyl disulfide under harsh conditions (Ph2S2–KOH, 1: 10, 75–80°C) makes it possible to obtain a mixture of six bis(phenylsulfanyl)butenes, 1,1-bis(phenylsulfanyl) but-1-ene being the major component. No bis(phenylselanyl) derivatives have been formed on heating up to 80°C. Dipotassium ethane-1,2-dithiolate reacts with 1,3-dichlorobut-2-ene to give a linear product of chlorine substitution at the sp3-carbon atom in two dichlorobutene molecules and a heterocyclic compound, 2-ethylidene-1,4-dithiane (a mixture of E and Z isomers), whose structure is different from the structure of the product obtained from 1,3-dichloropropene under analogous conditions. Mechanisms have been proposed for the formation of the isolated compounds.
Synthesis of polydentate chalcogen-containing ligands using the system hydrazine hydrate–base
Levanova,Vilms,Bezborodov,Babenko,Sosnovskaya,Istomina,Albanov,Russavskaya,Rozentsveig
, p. 396 - 401 (2017/05/01)
The reaction of dichlorodiethyl ether or dichlorodiethylamine hydrochloride with potassium or ethanolammonium dichalcogenides prepared in situ from elemental sulfur or selenium in the system hydrazine hydrate–alkali results in oligomeric dichalcogenides,
Effect of chalcogenyl substituent on the course of allyl rearrangement at chalcogenation of 1,3-dichloropropene
Levanova,Nikonova,Grabel’nykh,Russavskaya,Albanov,Rozentsveig,Korchevin
, p. 615 - 623 (2016/07/06)
Formation of 1,3-dichalcogenylpropene at the treatment of 1,3-dichloropropene with organic dichalcogenides in a redox system hydrazine hydrate–KOH is governed by the possibility of an allyl rearrangement. In the presence of bases this rearrangement proceeds via carbanion partially stabilized by the chalcogenyl substituent. The effectivity of the stabilization and consequently the probability of the rearrangement varies in the series of substituents PhS > BnS > PhSe. In the stage of the direct nucleophilic substitution of chlorine the anion PhSe?possesses the highest activity.
Chalcogenation of 1,4-dichlorobut-2-yne with organic dichalcogenides in the system hydrazine hydrate–KOH
Levanova,Vakhrina,Grabel’nykh,Rozentsveig,Russavskaya,Albanov,Klyba,Korchevin
, p. 2083 - 2089 (2016/10/03)
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.
Utility of a redox-active pyridine(diimine) chelate in facilitating two electron oxidative addition chemistry at uranium
Kiernicki, John J.,Fanwick, Phillip E.,Bart, Suzanne C.
supporting information, p. 8189 - 8192 (2014/07/21)
Exposure of the uranium(iv) complex, CpPU(MesPDI Me) (1) (MesPDIMe = 2,6-((Mes)NCMe) 2-C5H3N; Mes = 2,4,6-trimethylphenyl; Cp P = 1-(7,7-dimethylbenzyl)cyclopentadienyl), which contains a [ MesPDIMe]3- chelate, to I2, Cl 2, PhSeCl, and PhEEPh (E = S, Se, Te) results in oxidative addition to form the uranium(iv) family, CpPU(XX′)( MesPDIMe) (X = X′ = I, Cl, EPh; X = SePh, X′ = Cl). Spectroscopic and structural studies support products with [ MesPDIMe]1-, indicating the reducing equivalents derive from this redox-active chelate. This journal is the Partner Organisations 2014.
Mechanism and stereochemistry of domino reaction of 2,3-dichloroprop-1-ene with diphenyl dichalcogenides in the system hydrazine hydrate - KOH
Levanova,Vakhrina,Grabel'Nykh,Rozentsveig,Russavskaya,Albanov,Korchevin
, p. 1722 - 1727 (2015/05/20)
A new scheme of the domino reactions of diphenyl dichalcogenides with 2,3-dichloroprop-1-ene in the system hydrazine hydrate - KOH was suggested, which included nucleophilic substitution of the allylic chlorine atom in dichloropropene, dehydrochlorination of the product obtained with the formation of an allene derivative, addition of a nucleophile to the allene system, allene-acetylene rearrangement, addition of a nucleophile to the triple bond with the formation of a Z-adduct, isomerization of a 2,3-dichalcogenide product to Z-1,2-dichalcogenylprop-1-enes, and isomerization of Z-adducts to E-isomers. The most plausible mechanisms of individual steps, involving carbanions stabilized by the α-chalcogen atom, were considered.
New approaches to synthesis of unsaturated organochalcogen compounds with two different chalcogen atoms
Levanova,Vakhrina,Grabel'Nykh,Rozentsveig,Russavskaya,Albanov,Sanzheeva,Korchevin
, p. 2130 - 2137 (2015/02/19)
Two approaches to synthesis of bis-chalcogenyl derivatives of propene with two different chalcogen atoms are proposed. Reaction of 2,3-dichloro-1-propene with two different chalcogen nucleophiles PhY- (Y = S, Se) results in a mixture of two pro
Synthesis of unsaturated organoselenium compounds via the reaction of organic diselenides with 2,3-dichloro-1-propene in the hydrazine hydrate-KOH system
Levanova,Grabel'Nykh,Vakhrina,Russavskaya,Albanov,Klyba,Tarasova,Rozentsveig,Korchevin
, p. 1660 - 1665 (2013/11/19)
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, ca
