7392-11-2Relevant academic research and scientific papers
Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides
Levanova,Nikonova,Rosentsveig,Russavskaya,Albanov,Korchevin
, p. 1186 - 1190 (2017/09/29)
Reaction of 1,1- and 1,2-dichloroethenes with Ph2S2, Ph2Se2, Bn2S2, and i-Pr2S2 in a system hydrazine hydrate–KOH proceeds as a sequence of successive transformations: dehydrochlorination of initial dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile (ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond affording 1,2- dichalcogenylethenes. In reactions with PhS– and PhSe? nucleophiles due to the high rate of all stages 1,2-bis (phenylchalcogenyl)ethenes are obtained having mainly the Z-configuration. In reactions with BnS? and i-PrS? in the IR, NMR and chromato-mass spectra intermediate ethynylchalcogenides were identified, and the final products consisted of a mixture with the prevalence of the Z-isomer.
Synthesis of vinyl thioethers and bis-thioethenes from calcium carbide and disulfides
Rodygin, Konstantin S.,Gyrdymova, Yuliya V.,Zarubaev, Vladimir V.
, p. 476 - 478 (2017/10/05)
Bis-thioethenes and vinyl thioethers were obtained from the reaction of disulfides and calcium carbide in good to high yields using a simple synthetic procedure and common laboratory setup. The tolerance of the reaction was investigated by the examples of aliphatic, aromatic, heteroaromatic and sesquiterpenic substrates.
A recyclable biphasic system for stereoselective and easily handled hydrochalcogenations
Tidei, Caterina,Sancineto, Luca,Bagnoli, Luana,Battistelli, Benedetta,Marini, Francesca,Santi, Claudio
supporting information, p. 5968 - 5975 (2015/03/30)
Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, ste
Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes
Perin, Gelson,Borges, Elton L.,Alves, Diego
experimental part, p. 2066 - 2069 (2012/07/14)
The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH4 in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields.
Rhodium-Catalyzed Regio- and Stereoselective 1-Seleno-2-thiolation of 1-Alkynes
Arisawa, Mieko,Kozuki, Yoshihiro,Yamaguchi, Masahiko
, p. 8964 - 8967 (2007/10/03)
Rhodium complex RhH(PPh3)4 and 1,1′-bis(diphenylphosphino)ferrocene catalyze the regio- and stereoselective additions of diaryl disulfides and diaryl diselenides to 1-alkynes giving (Z)-1-arylseleno-2-arylthio-1-alkenes. The catalyst promotes the addition reaction of dibutyl disulfide and dibutyl diselenide to 1-octyne with a similar selectivity giving (Z)-1-butylseleno-2-butylthio-1-octene but with a lower catalytic activity. The same product is obtained with a higher yield, when excess dibutyl disulfide is used against dibutyl diselenide in the presence of RhH(PPh3)4 and 1,4-diphenylphosphinobutane.
Synthesis of Vinyl Selenides or Sulfides and Ketene Selenoacetals or Thioacetals by Nickel(II) Vinylation of Sodium Benzeneselenolate or Benzenethiolate
Cristau, H. J.,Chabaud, B.,Labaudiniere, R.,Christol, H.
, p. 875 - 878 (2007/10/02)
The substitution of bromine atom on a double bond by benzeneselenolate or benzenethiolate anions is catalyzed by the bis(pyridine)nickel bromide complex.Various alkenyl selenides or sulfides and seleno- or thio acetals are prepared in good to excellent yi
NEW SYNTHESIS OF VINYL SELENIDES NUCLEOPHILIC SUBSTITUTIONS OF UNACTIVATED VINYL HALIDES BY SELENIDE ANIONS
Tiecco, M.,Testaferri, L.,Tingoli, M.,Chianelli, D.,Montanucci, M.
, p. 4975 - 4978 (2007/10/02)
Alkyl and aryl selenide anions react with unactivated vinyl halides, in dipolar aprotic solvents, to give alkyl or aryl vinyl selenides in good yields.These reactions are stereospecific and occur with retention of configuration.
SYNTHESIS, PROPERTIES, AND MULTINUCLEAR (1H, 13C, 77Se) NUCLEAR MAGNETIC RESONANCE STUDIES OF SELENOETHERS CONTAINING TWO OR MORE SELENIUM ATOMS
Gulliver, David J.,Hope, Eric G.,Levason, William,Murray,Stephen G.,Potter, David M.,Marshall, Gregory L.
, p. 429 - 434 (2007/10/02)
A convenient synthesis of MeSeLi from MeLi and Se8 in tetrahydrofuran (THF) has been used to prepare the bis-selenoethers MeSenSeMe (n = 1,2,3,6, or 12) and cis-MeSeCH=CHSeMe.PhSenSePh (n = 1-3) and cis-PhSeCH=CHSePh have been prepared from PhSe-, itself produced from Ph2Se2 and LiALH4-THF or sodium hydroxymethanesulphinate.The bis-selenoethers o-C6H4(SeR)2 (R = Me or Ph) were obtained from R2Se2 and benzyne.The syntheses of (RSeCH2)3CMe (R = Me or Ph), (MeSeCH2)4C, and (MeSeCH2CH2CH2)2Se are also described.The 1H, 13C, and 77Se n.m.r. spectra of these selenoethers have been recorded, and the chemical shifts and coupling constants (nJSe-H, nJSe-C) are discussed in terms of structures.Mass spectra of the selenoethers have been recorded and the principle fragmentation modes identified.
