814-22-2Relevant academic research and scientific papers
The Atherton-Todd reactions under sonochemical activation
Oussaid,Soufiaoui,Garrigues
, p. 871 - 875 (1995)
Alcohols 1a-g phosphorylation is performed in the Atherton-Todd reaction conditions (mixture of diethylphosphonate and carbone tetrachloride and triethylamine under ultrasonic irradiation). The expected phosphates 2a-g are obtained in good yields.
Kinetics and adsorption calculations: insights into the MgO-catalyzed detoxification of simulants of organophosphorus biocides
Almerindo, Gizelle I.,Buratto, Suelen C.,Caramori, Giovanni F.,Fiedler, Haidi D.,Medeiros, Michelle,Micke, Gustavo A.,Nicolazi, Lucas M.,Nome, Faruk,Parreira, Renato L. T.,Sangaletti, Patrícia,Schneider, Felipe S. S.,Wanderlind, Eduardo H.
, p. 19011 - 19021 (2020/10/02)
We report the targeted decomposition of the organophosphate methyl paraoxon by means of its transesterification with 1-propanol catalyzed by magnesium oxide. Catalyst characterization by energy dispersive X-ray fluorescence (EDXRF), nitrogen adsorption/desorption measurements (BET and BJH methods), and temperature programmed desorption of CO2(CO2-TPD) showed that the employed MgO presents properties favorable for the methyl paraoxon adsorption and transesterification to occur. A thorough kinetic investigation showed that rate enhancements up to 3 × 106-fold can be achieved in comparison with the spontaneous propanolysis of the substrate, and that the material can be used in additional cycles without loss of catalytic activity, with the catalyst recovery achieved through a simple washing procedure. Energies for adsorption of 1-propanol and methyl paraoxon onto a MgO model surface were obtained by density functional theory calculations, which showed that the latter displays a stronger affinity for the catalyst surface, and that the reaction should proceed with methyl paraoxon and 1-propanol molecules juxtapositioned at adjacent Mg2+sites, with nucleophilic and electrophilic centersca.2.4 ? away from each other. Additionally, MgO also promoted rate enhancements up to 5 × 104-fold in the propanolysis of a further range of representative phosphate triesters, and in most of the cases the final transesterified products are trialkyl phosphates structurally related to a family of flame-retardants. The results thus provide insights into the development of novel systems for the targeted conversion of organophosphorus compounds into value-added products by employing simple, highly efficient, and low-cost metal oxide catalysts.
LiI/TBHP Mediated Oxidative Cross-Coupling of P(O)–H Compounds with Phenols and Various Nucleophiles: Direct Access to the Synthesis of Organophosphates
Anitha, Thippani,Ashalu, Kashamalla Chinna,Sandeep, Mummadi,Mohd, Aabid,Wencel-Delord, Joanna,Colobert, Francoise,Reddy, Kallu Rajender
, p. 7463 - 7474 (2019/12/03)
An efficient and mild method for the direct phosphorylation of phenols, alcohols, and amines with P(O)–H has been reported by LiI/TBHP mediated oxidative cross-coupling reaction. Moreover, this protocol extended to β-keto esters for the synthesis of enol phosphates using H-phosphonates. Notably, this developed method applied for the synthesis of organopesticides such as paraoxon, cyanophos, and methyl parathion. The key features of this protocol are mild conditions, short reaction time, good functional group tolerance, and broad substrate scope.
Method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction
-
Paragraph 0031, (2018/12/14)
The invention belongs to the technical field of organic synthesis, discloses a method for synthesis of organophosphorus compound by photo-induced iodine catalyzed Atherton-Todd reaction. The method comprises the following steps: a compound shown as formula II and a nucleophilic reagent are subjected to reaction for 24 hours in a dichloromethane solvent, an oxygen atmosphere, under irradiation condition of room temperature and the action of a halogenated reagent I2, then the organophosphorus compound shown as the formula II is obtained through washing, drying, separating and purifying. According to the the method provided by the invention, compared with traditional Atherton-Todd reaction, no catalysis of metal is needed,no addition of alkali is needed, reaction environment such as metal, high temperature and strong base is replaced, a series of organophosphorus compounds can be synthesized by catalyzing a variety of substrates under the irradiation condition of room temperature, and hasthe advantages of good universality, short reaction time and higher yield.
Cross-hetero-dehydrogenative coupling reaction of phosphites: A catalytic metal-free phosphorylation of amines and alcohols
Dhineshkumar, Jayaraman,Prabhu, Kandikere Ramaiah
supporting information, p. 6062 - 6065 (2014/01/06)
Phosphorylation of amines, alcohols, and sulfoximines are accomplished using molecular iodine as a catalyst and H2O2 as the sole oxidant under mild reaction conditions. This method provides an easy route for synthesizing a variety of phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates which are of biological importance.
Synthesis of mixed alkylphosphites and alkylphosphates
Ilia, Gheorghe,Popa, Adriana,Iliescu, Smaranda,Bora, Alina,Dehelean, Gheorghe,Pascariu, Aurelia
, p. 1513 - 1519 (2007/10/03)
Some mixed phosphites having two different alkyl chain were obtained as forerunners for mixed phosphates Mixed dialkyl phosphates were obtained in good yields (40-80%) by phase transfer catalysis in liquid-liquid sistem, starting from different dialkyl phosphites and aliphatic alcohols. The reaction conditions were optimized in order to obtain good yields in phosphites and phosphates respectively. Compounds were analyzed by IR, P31-NMR.
REACTION OF PROPOSED PHOSPHOROTHIOLATE S-OXIDE INTERMEDIATES WITH ALCOHOLS
Segall, Yoffi,Casida, John E.
, p. 209 - 212 (2007/10/02)
S-Oxide 2 is an extremely reactive intermediate.Its phosphorylation vs rearrangement rates, strongly depend upon the nature of the nucleophile.
