18893-62-4Relevant academic research and scientific papers
Reactivity of 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) with O-nucleophiles generated by potassium tert-butoxide
Pellizzaro, Leonardo,Cabianca, Elena,Tatibou?t, Arnaud,Padovan, Pierluigi,Fabris, Fabrizio,Rollin, Patrick,De Lucchi, Ottorino
, p. 3699 - 3703 (2007)
E-1-Phenylsulfinyl-2-phenylsulfanylethylene (E-SOSE) reacts with O-nucleophiles generated by means of t-BuOK via an addition-elimination mechanism, thus affording the product of substitution of the phenylsulfanyl group in a stereo-conservative process. When used alone, the strongly basic and hindered tert-butoxide brings about elimination of either the phenylthiolate or phenylsulfinate groups. Z-SOSE is much more prone to elimination: either with t-BuOK alone or with other O-nucleophiles generated by t-BuOK, it always leads to products derived from elimination. Other alkaline tert-butoxides or other bases appear not as effective in generating species nucleophilic enough to react with E-SOSE.
An alternative, inexpensive preparation of phenylsulfonylethylene
Cossu, Sergio,De Lucchi, Ottorino,Durr, Richard,Fabris, Fabrizio
, p. 211 - 216 (1996)
The reaction of (Z)-1,2-bis(phenylsulfonyl)ethylene with tributyltin hydride gives quantitatively phenylsulfonylethylene and constitutes an alternative and inexpensive preparation of this widely used reagent. The reaction also occurs with silicon hydrides (Pd catalyst) and sodium borohydride but the former reaction is not as clean as with tin hydridese while the latter gives the over reduced product phenylsulfonylethane.
Application of Ni-based metal-organic framework as heterogeneous catalyst for disulfide addition to acetylene
Ananikov, Valentine P.,Degtyareva, Evgeniya S.,Erokhin, Kirill S.
, (2020/08/05)
Several recent studies have shown unique adsorption activity of metal organic frameworks (MOFs) towards unsaturated hydrocarbons. In the current article, we explored the application of Ni-MOFs for S-functionalization of acetylene. We showed that Ni-MOF-74 catalyzed the reaction of disulfide addition to gaseous acetylene with excellent selectivity. The prime advantage of the proposed Ni-MOF-74 over other examined catalysts was its easy separation and recycling possibility. Moreover, it demonstrated no leaching of Ni species into the solution. The work was supplemented with a study on the catalyst behavior in the course of the reaction by using SEM, EDX, XRD, and FT-IR methods.
Switchable Ni-catalyzed bis-thiolation of acetylene with aryl disulfides as an access to functionalized alkenes and 1,3-dienes
Degtyareva, Evgeniya S.,Erokhin, Kirill S.,Kashin, Alexey S.,Ananikov, Valentine P.
, p. 170 - 179 (2019/01/04)
The article provides the first example of metal-catalyzed aryl disulfide addition to unsubstituted acetylene. The use of inexpensive Ni(acac)2 precatalyst with phosphine ligands results in competitive formation of (Z)-1,2-bis(arylthio)ethenes a
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.
An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source
Rodygin, Konstantin S.,Ananikov, Valentine P.
supporting information, p. 482 - 486 (2016/01/30)
Chemical reactions involving high-pressure acetylene are not easily performed in a standard laboratory setup. The risk of explosion and technical difficulties drastically complicate the equipment and greatly increase the cost. In this study, we propose th
SINGLET OXYGEN-LABILE LINKERS AND METHODS OF PRODUCTION AND USE THEREOF
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Paragraph 000156, (2013/11/18)
Activatable compositions that include at least one functional moiety and at least one cleavable linker directly or indirectly linked to the at least one functional moiety are disclosed. The at least one functional moiety is inactive when linked to the linker and activated upon cleavage of the linker. Methods of production and use of the activatable composition are also disclosed.
Click and photo-unclick chemistry of aminoacrylate for visible light-triggered drug release
Bio, Moses,Nkepang, Gregory,You, Youngjae
supporting information; experimental part, p. 6517 - 6519 (2012/07/28)
"Click and Photo-unclick Chemistry" of aminoacrylates is proposed for a new photo-labile linker. Adducts are built in 2 steps with good yields and cleaved rapidly by tissue penetrable visible light (690 nm) with a photosensitizer. Facile synthesis, release of mother drug, and stability and cleavage in medium are demonstrated.
DTBB-catalysed lithiation of 1,2-bis(phenylsulfanyl)ethene: Does 1-lithio-2-phenylsulfanylethene really exist?
Gómez, Cecilia,Maciá, Beatriz,Yus, Miguel
, p. 9325 - 9330 (2007/10/03)
The reaction of (Z)- or (E)-1,2-bis(phenylsulfanyl)ethene (1) with an excess of lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 2.5 mol%) in the presence of a carbonyl compound as electrophile (Barbier conditions) in THF at -78°C leads, after hydrolysis with water at temperatures ranging between -78°C and rt, to a mixture of the corresponding (Z/E)-unsaturated 1,4-diols 2, the diastereomers ratio being independent of the stereochemistry of the starting materials. Allylic alcohols 3 are the main by-products, resulting from a lithium-hydrogen exchange on some of the lithiated intermediates along the whole process. A mechanistic explanation for the observed behaviour is given.
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.
