29507-64-0Relevant academic research and scientific papers
Convenient one-pot syntheses of 1,2-dithiole-3-thiones and 3-imino-1,2-dithioles from terminal alkynes
Adams, Harry,Hughes, Amelia J.,Morris, Michael J.,Quenby, Sophia I.A.
, p. 5283 - 5285 (2015/02/02)
The reaction of acetylide anions with carbon disulfide or phenyl isothiocyanate followed by addition of sulfur in the presence of a protonating agent such as a primary amine or alcohol affords 1,2-dithiole-3-thiones or 3-imino-1,2-dithioles in good to excellent yields.
Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane
Curphey, Thomas J.
, p. 6461 - 6473 (2007/10/03)
The combination of P4S10 and hexamethyldisiloxane efficiently converts esters, lactones, amides, lactams, and ketones to their corresponding thiono derivatives. In the presence of elemental sulfur, 3-oxoesters are converted to dithiolethiones by this reagent. Yields are comparable to or superior to those obtained with Lawesson's reagent. The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent.
A superior procedure for the conversion of 3-oxoesters to 3H-1,2-dithiole-3-thiones
Curphey
, p. 9963 - 9966 (2007/10/03)
The combination of P4S10, sulfur, and hexamethyldisiloxane converts 3-oxoesters to 3H-1,2-dithiole-3-thiones in yields generally superior to those obtained with Lawesson's reagent and without the need for chromatography to remove large amounts of phosphorous-containing byproducts. (C) 2000 Elsevier Science Ltd.
Dianions of 3-oxodithioic acids: Preparation and conversion to 3H-1,2-dithiole-3-thiones
Curphey,Libby
, p. 6977 - 6980 (2007/10/03)
Reaction of ketones with CS2 and 2 equivalents of KH in THF-N,N'-dimethylpropyleneurea solution produces the dianions of 3-oxodithioic acids. These dianions are converted in good yield to 3H-1,2-dithiole-3-thiones by the sequential action of hexamethyldisilathiane and an oxidizing agent such as hexachloroethane. (C) 2000 Elsevier Science Ltd.
A New Synthesis of 3H-1,2-Dithiole-3-thiones
Curphey, Thomas J.,Joyner, H. Howard
, p. 3703 - 3706 (2007/10/02)
Exposure of 3-oxo dithioic acids to a solution of polysulfanes in liquid hydrogen sulfide gives 3H-1,2-dithiole-3-thiones in yields varying from poor to excellent.The method tolerates the presence of functional groups which are problematical for other met
Synthesis of 3H-1,2-dithiole-3-thiones by a novel oxidative cyclization
Curphey, Thomas J.,Joyner, H. Howard
, p. 7231 - 7234 (2007/10/02)
Reaction of 3-oxo dithioic acids with a combination of hexamethyldisilathiane and N-chlorosuccinimide in the presence of a catalytic amount of imidazole brings about oxidative ring closure to 3H-1,2-dithiole-3-thiones. Yields vary from poor to good.
A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects, Respectively, by Sulfuration of Alkynes with Elemental Sulfur
Choi, Keun Soo,Akiyama, Isao,Hoshino, Masamatsu,Nakayama, Juzo
, p. 623 - 629 (2007/10/02)
Sulfuration of a series of alkynes by elemental sulfur was investigated.Alkynes carrying highly bulky substituents, 2,2,5,5-tetramethyl-3-hexyne (6a), 1,2-di-(1-adamantyl)ethyne (6b), 3,3-dimethyl-1-phenyl-1-butyne (6c), and 1-(1-adamantyl)-2-phenylethyne (6d), reacted with sulfur to give the corresponding stable 1,2-dithietes 7a-d in 46-65percent yields.Less hindered alkynes reacted with sulfur to afford 1,4-dithiins and thiophenes as the final products which were derived from the initial products, 1,2-dithietes, via their tautomerization to the corresponding 1,2-dithioxo compounds, while extremely congested alkynes failed to react with sulfur even under forcing conditions.On the other hand, ynamines, a typical electron-rich alkyne, 1-diethylamino-2-phenylthioethyne (6o), 1-diethylamino-2-phenylselenoethyne (6p), and tetraethylethynediamine (6q) were sulfurated under milder conditions to afford resonance-stabilized 1,2-dithioxo compounds 19o-q as the principal products.Mechanism of the formation of 1,2-dithietes, 1,2-dithioxo compounds, and other products is discussed.
A convenient synthesis of 1,2-dithietes and α-dithiocarbonyl compounds by sulfuration of acetylenic compounds
Nakayama, Juzo,Choi, Keun Soo,Akiyama, Isao,Hoshino, Masamatsu
, p. 115 - 118 (2007/10/02)
Di-tert-butyl-, di-1-adamantyl-, 1-(1-adamantyl)-2-tert-butyl-, and 1-(1-adamantyl)-2-phenylacetylenes react with elemental sulfur.
