20979-95-7Relevant academic research and scientific papers
Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
De La Vega-Hernández, Karen,Senatore, Raffaele,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 1970 - 1978 (2019/02/20)
Thioformamides are easily prepared-under full chemocontrol-through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.
Studies on organophosphorus compounds. XLV. Thiation of some sterically hindered N-nitrosamides
Joergensen, Karl Anker,Ghattas, Abdul-Badik,Lawesson, Sven-Olov
, p. 204 - 208 (2007/10/02)
Some sterically hindered N-nitrosamides have been prepared using sodium nitrite in aqueous acid solution.Reaction of these N-nitrosamides with 2,4-bis-(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane-2,4-disulfide (Lawesson's Reagent ) causes thiation of both the carbonyl and the nitroso groups followed by destruction of the nitroso group giving ultimately the corresponding thioamides and amides as the main products.Dihydro-2(3H)-thiophenone is isolated as a by-product when N-nitroso-dihydro-2(3H)-pyrrolidinone is reacted with LR.A mechanism for its formation is postulated.Thiation of the sterically hindered amides yields the thioamide as rotamers which in two cases could be separated by column chromatography.Ames test has been performed for some of the compounds.
