20890-80-6Relevant academic research and scientific papers
Method for preparing aryl vinyl alkyl thioether through C/C-S monatomic assembly process
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Paragraph 0095; 0100-0101; 0115-0117, (2022/04/08)
The invention discloses a method for preparing aryl vinyl alkyl thioether through a C = C-S monatomic assembly process, which comprises the following steps: respectively providing an atom for a C = C-S structure by dimethyl sulfoxide, aromatic aldehyde ketone and sulfur-containing reagent sodium mercaptide/dithioether under the action of air atmosphere and alkali; the construction process is completed by one-pot reaction, and the product aryl vinyl alkyl thioether compound is obtained. The aryl vinyl of the aryl vinyl alkyl thioether compound prepared by the method comes from aromatic aldehyde ketone, but a double-bond carbon atom is added compared with the original aromatic aldehyde ketone raw material, and the method has the advantages of wide and easily available raw material source, environmental protection, low price, simple operation and facilitation of industrial production.
N-heterocyclic carbene-catalyzed regio- and stereoselective hydrothiolation reaction of alkynes
Cong, Zi-Song,Zhang, Yang,Du, Guang-Fen,Gu, Cheng-Zhi,He, Lin
supporting information, p. 1838 - 1846 (2018/06/25)
N-heterocyclic carbenes (NHCs) have been utilized as Br?nsted base to catalyze the hydrothiolation reaction between alkynes and thiols to produce the vinyl sulfides stereoselectively.
Stereoselective heck reactions with vinyl sulfoxides, sulfides and sulfones
Bachmann, Daniel G.,Wittwer, Christopher C.,Gillingham, Dennis G.
supporting information, p. 3703 - 3707 (2014/01/06)
We report the Heck cross-coupling of notoriously unreactive, but synthetically valuable olefins: vinyl sulfoxides, vinyl sulfones, and vinyl sulfides. Key findings include the importance of the sterically hindered (tri-tert-butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, E-selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry. Copyright
Ionic liquid promoted regio- And stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Ghosh, Sudip,Jana, Ranjan
experimental part, p. 1199 - 1204 (2009/12/31)
A simple ionic liquid, l-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, promotes anti-Markovnikov addition of thiols to alkynes providing (Z)- and (E)-vinyl sulfides stereoselectively. The addition of thiols to alkenes in presence of another ionic liquid, [pmim]Br proceeds through anti-Markovnikov manner, whereas the addition to vinyl ethers and acetates occurs at more electrophilic C-2 position adjacent to oxygen. The products are obtained in high yields.
Heck vinylations using vinyl sulfide, vinyl sulfoxide, vinyl sulfone, or vinyl sulfonate derivatives and aryl bromides catalyzed by a palladium complex derived from a tetraphosphine
Battace, Ahmed,Zair, Touriya,Doucet, Henri,Santelli, Maurice
, p. 3495 - 3505 (2008/02/10)
The adverse impact of sulfur compounds on catalytic performance is well known. The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis[(diphenylphosphino) methyl]cyclopentane in combination with allylchloropalladium dimer affords an efficient catalyst for the Hec
Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides
Aitken, R. Alan,Armstrong, Jill M.,Drysdale, Martin J.,Ross, Fiona C.,Ryan, Bruce M.
, p. 593 - 604 (2007/10/03)
A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.
Mn(III)-based reactions of alkenes and alkynes with thiols. An approach toward substituted 2,3-dihydro-1,4-oxathiins and simple route to (E)-vinyl sulfides
Nguyen, Van-Ha,Nishino, Hiroshi,Kajikawa, Shougo,Kurosawa, Kazu
, p. 11445 - 11460 (2007/10/03)
The first example using manganese(III) acetate in the reaction of 1,1- diarylethenes with α-mercaptoketones was examined. A mixture of the ethenes and α-mercaptoketones was treated with manganese(III) acetate in acetic acid, affording cycloaddition products in moderate yields, together with substituted products. The reaction may involve the formation of a carbonation and subsequent cyclization to give the substituted 2,3-dihydro-1,4-oxathiin 3. A similar reaction with thioglycolic acid gave 1,4-oxathiolan-2-one 7. While thiyl radicals easily formed by manganese(III) oxidation with ethanethiol or benzenethiol reacted with alkynes to give preferentially (E)- vinyl sulfides 10 in quantitative yields.
REACTION OF ETHYLTRITHIOCARBONATE AND TRITHIOCARBONATE IONS WITH ACETYLENES
Ivanova, N. I.,Sigalov, M. V.,Amosova, S. V.,Trofimov, B. A.
, p. 451 - 454 (2007/10/02)
When heated with phenylacetylene in aqueous THF, potassium ethyltrithiocarbonate forms 1-phenyl-1-ethylthioethene in addition to cis-1-phenyl-2-ethylthioethene.The reaction takes place in DMSO, dioxane, benzene, and ethanol.It was established that cis-1-phenyl-2-ethylthioethene is formed exclusively in DMSO and 1-phenyl-1-ethylthioethene is formed in benzene.The reaction of potassium trithiocarbonate with ethylene in DMSO leads to divinyl sulfide.
