87373-88-4Relevant academic research and scientific papers
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions
Castoldi, Laura,Di Tommaso, Ester Maria,Gr?fen, Barbara,Olofsson, Berit,Reitti, Marcus
supporting information, p. 15512 - 15516 (2020/06/23)
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
Copper-catalyzed synthesis of vinyl sulfides
Bates, Craig G.,Saejueng, Pranorm,Doherty, Michael Q.,Venkataraman
, p. 5005 - 5008 (2007/10/03)
(Chemical Equation Presented) We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3) 2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.
NUCLEOPHILIC VINYLIC SUBSTITUTIONS ON UNACTIVATED SUBSTRATES. THE BEHAVIOUR OF STYRYL ALKYL SULPHIDES AND SELENIDES TOWARDS SULPHUR AND SELENIUM NUCLEOPHILES
Testaferri, L.,Tiecco, M.,Tingoli, M.,Chianelli, D.
, p. 1401 - 1408 (2007/10/02)
Sodium alkanethiolates or lithium methyl selenide react with styryl alkyl sulphides and selenides, in DMF at 100 deg C, to give the products of vinylic or aliphatic substitution.The two nucleophilic reagents are extremely selective.In the case of RSNa the
Nucleophilic Substitutions of Unactivated Vinyl Halides with Alkanethiolate Anions in Hexamethylphophoramide
Tiecco, Marcello,Testaferri, Lorenzo,Tingoli, Marco,Chianelli, Donatella,Montanucci, Manuela
, p. 4795 - 4800 (2007/10/02)
The reactions of unactivated vinyl halides with the sodium salts of alkanethiols in HMPA gave vinyl alkyl sufides in high yields.These reactions occur with complete retention of configuration.With di-, tri-, and tetrachloroethylenes all the chlorine atoms are substituted by alkylthio groups.By treatment with alkanethiolates the vinyl sulfides are dealkylated to give the sodium salts of the ene thiols.By reaction with sodium all the alkylthiogroups present in the molecule suffer fragmentation to give the sodium salts of the corresponding mercaptoethylenes.
