3096-08-0Relevant articles and documents
Unexpected Z/E isomerism of N-methyl-O-phosphothioyl benzohydroxamic acids, their oxyphilic reactivity and inertness to amines
Majewski, Arkadiusz,Chojnacki, Jaros?aw,Przychodzeń, Witold
, p. 1077 - 1091 (2021/01/11)
Thiophosphinoylation of N-methyl p-substituted benzohydroxamic acids using disulfanes (method A) or diphenylphosphinothioyl chloride (method B) provides only one conformer of the respective O-phosphothioyl derivative (X-ray and NMR analysis). Undergoing t
1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds - A kinetic comparative study
Ponomarov, Oleksandr,Laws, Andrew P.,Hanusek, Ji?í
supporting information, p. 8868 - 8876 (2013/01/15)
The sulfurization efficiency of 25 3-substituted-1,2,4-dithiazole-5-ones and 5-thiones towards triphenyl phosphite in acetonitrile, DCM, THF and toluene at 25 °C was evaluated. All the 1,2,4-dithiazoles are much better sulfurizing reagents than commercially available agents (PADS, TETD, Beaucage's reagent). The most efficient sulfurizing agents in all solvents are 3-phenoxy (4), 3-phenylthio (5) and 3-ethoxy-1,2,4-dithiazole-5-one (1) whose reactivity is at least two orders of magnitude higher than that of other 1,2,4-dithiazoles. Contrary to a previous report, the sulfurization with 1 does not yield carbonylsulfide and ethyl cyanate as the additional reaction products but unstable ethoxythiocarbonyl isocyanate which has been trapped with 4-methoxyaniline. Similar trapping experiments have proven that the site of attack is at the sulfur adjacent to the CO group for compounds 4 and 5. The reaction pathway involves rate-limiting initial nucleophilic attack of the phosphorus at sulfur followed by decomposition of the phosphonium intermediate to the corresponding phosphorothioate and isocyanate/isothiocyanate species. The existence of the phosphonium intermediate during sulfurization of triphenyl phosphine with 3-phenyl-1,2,4-dithiazole-5-thione (7a) was proven using kinetic studies. From the Hammett and Bronsted correlations and from other kinetic measurements it was concluded that the transition-state structure is almost apolar for the most reactive 1,2,4-dithiazoles whereas a polar structure resembling a zwitter-ionic intermediate may be more appropriate for the least reactive 1,2,4-dithiazoles. The extent of P-S bond formation and S-S bond cleavage is very similar in all reaction series but it gradually decreases with the reactivity of the 1,2,4-dithiazole derivatives.
The aza-Morita-Baylis-Hillman reaction of N-thiophosphoryl imines catalyzed by 1,3,5-triaza-7-phosphaadamantane (PTA) - Convenient synthesis of α-methylene-β-amino ketone or acid derivatives
Xu, Xinyuan,Wang, Chungui,Zhou, Zhenghong,Tang, Xiaofang,He, Zhengjie,Tang, Chuchi
, p. 4487 - 4491 (2008/02/12)
In the presence of an effective air-stable nucleophilic trialkylphosphane orgaocatalyst, 1,3,5-triaza-7-phosphaadamantane, N-diethoxythiophosphorylimines 1 and N-diphenylthiophosphinoylimines 2 exhibited good reactivity in the methyl vinyl ketone or methy
The study of the reaction between thiophosphoryl esters and boron tribromide. The synthesis of oxathiaphosphaboretanes
Lewkowski, Jaroslaw,Mortier, Jacques,Vaultier, Michel
, p. 1 - 14 (2007/10/03)
Reactions between three thiophosphoryl esters and boron tribromide are reported. O,O,O-triethyl phosphorothionate (1) and O,O-diethyl methanephosphonothionate (5) gave substituted oxathiaphosphaboretanes 4 and 7 respectively. O-methyl diphenyl-phosphinothionate (9) led to the complex 11 and the corresponding oxathiaphosphaboretane 12. In order to establish the mechanism, reactions were monitored by the multinuclear NMR spectroscopy.
CONVERSION OF NITRILES TO THIOAMIDES UNDER THE ACTION OF THE BINARY THIONYLATING SYSTEM PHOSPHORUS DITHIOACID-ALCOHOL
Zabirov, N. G.,Shamsevaleev, F. M.,Cherkasov, R. A.
, p. 56 - 63 (2007/10/02)
Binary systems of phosphorus dithioacid-methanol and phosphorus pentasulfide-methanol are effective hydrosulfonating systems for the conversion of aromatic nitriles to the corresponding primary thioamides.In ternary systems nitrile-phosphorus dithioacid-alcohol from one to four parallel processes can occur.The structure of the phosphorus dithioacids has little effect, whereas the structures of the nitrile and alcohol substantially influence both the rate of the processes and the possible pathway.The reactivity of alcohols in these reactions drops with increasing volume of the hydrocarbon radical.
Phosphororganische Verbindungen 100. Thiophosphylverbindungen Durch P=O/P=S-Austausch
Horner, L.,Lindel, H.
, p. 259 - 262 (2007/10/02)
Phosphinic-acid-, phosphonic-acid- and phosphoric-acid-derivatives react in high yields with Lawesson's reagent to form the corresponding thiophosphyl-compounds.
