Green, catalyst-free thioacetalization of carbonyl compounds using glycerol as recyclable solvent
We describe herein the use of glycerol as an efficient and a recyclable solvent in the thioacetalization of aldehydes and ketones. The catalyst-free reactions proceed easily using glycerol at 90 °C and the corresponding thioacetals were obtained in good to excellent yields. Glycerol was recovered and utilized for further thioacetalization reactions.
Perin, Gelson,Mello, Luzia G.,Radatz, Cátia S.,Savegnago, Lucielli,Alves, Diego,Jacob, Raquel G.,Lenard?o, Eder J.
experimental part
p. 4354 - 4356
(2010/09/12)
Selenonium ionic liquid as an efficient catalyst for the synthesis of thioacetals under solvent-free conditions
Acidic ionic liquid butyl ethyl phenyl selenonium tetrafluoroborate, [BEPSe]BF4, was successfully employed as a catalyst for the synthesis of several dithioacetals in the absence of a solvent. The method is general and selectively afforded thioacetals derived from aldehydes and ketones in good yields.
Lenard?o, Eder J.,Borges, Elton L.,Mendes, Samuel R.,Perin, Gelson,Jacob, Raquel G.
p. 1919 - 1921
(2008/09/19)
Anodic gem-Difluorination of Dithioacetals
Anodic desulfurization of dithioacetals of ketones in the presence of Et3N*3HF provided the corresponding gem-difluorocompounds while dithioacetals of aromatic and aliphatic aldehydes gave gem-difluorothioethers and monofluoro thioether, respectively.
Yoshiyama, Tomonori,Fuchigami, Toshio
p. 1995 - 1998
(2007/10/02)
Reactions of Triplet Carbenes with Sulfides and Disulfides: Ylide vs. Radical Formation
The reactions between triplet diphenylcarbene and fluorenylidene with a variety of sulfides and disulfides were investigated with use of electron paramagnetic resonance (EPR) spectroscopy, laser flash photolysis, and product studies.Diphenylcarbene reacted with these substrates by a radical-like displacement mechanism.Rate constants were ca. 1E6 M-1 s-1, and the resulting thio-substituted diphenylmethyl radicals were identified by their EPR and optical spectra.By contrast, the analogous reactions of fluorenylidene had rate constants of 1E8-1E9 M-1 s-1 and proceeded by an ylide mechanism.Product studies were consistent with these results but were not sufficient in themselves to reveal these mechanistic differences.
Alberti, A.,Griller, D.,Nazran, A. S.,Pedulli, G. F.
p. 3024 - 3028
(2007/10/02)
FACILE SYNTHETIC METHODS OF ACETALS AND CROWN ETHERS FROM THE REACTION OF DIPHENYLDIAZOMETHANE WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE IN THE PRESENCE OF ALCOHOLS
The reaction of diphenyldiazomethane with 2,3-dichloro-5,6-dicyanobenzoquinone in the presence of alcohols and thiols gave the corresponding benzophenone acetals and thioacetals at 20-25 deg C in 1,2-dichloroethane.The mechanism of the reaction will be discussed.
Oshima, Takumi,Nishioka, Ryoji,Nagai, Toshikazu
p. 3919 - 3922
(2007/10/02)
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