18755-43-6Relevant articles and documents
Fragmentation-Related Phosphonylation of Nucleophiles Utilizing P-Alkyl 2,3-oxaphosphabicyclo[2.2.2]octene 3-oxide Precursors
Kovács, Tamara,Fül?p, Laura Szandra,Keglevich, Gy?rgy
, p. 83 - 90 (2016)
New P-alkyl 2,3-oxaphosphabicyclo-[2.2.2]octene 3-oxides were synthesized by the Bayer-Villiger oxidation of the corresponding 7-phosphanorbornene 7-oxides and were used as precursors for reactive alkylmetaphosphonates useful in the phosphonylation of alcohols. This is the first case that the reactivity of the two regioisomers formed by O-insertion was differentiated and that the fragmentation-related phosphonylation leading to phosphonic acid-esters was achieved under microwave-assisted conditions.
An optimized and scalable synthesis of propylphosphonic anhydride for general use
Pizova, Hana,Bobal, Pavel
supporting information, p. 2014 - 2017 (2015/03/30)
Abstract Propylphosphonic anhydride (T3P) is an effective coupling and dehydrating agent, which has been used for a large number of chemical transformations. An efficient and versatile synthetic method is described to synthesize propylphosphonic anhydride (T3P) in pure form, in an overall yield of 51% in four steps from commercially available diethyl phosphonate.
Mild and efficient esterification of alkylphosphonic acids using polymer-bound triphenylphosphine
Purohit, Ajay Kumar,Pardasani, Deepak,Tak, Vijay,Kumar, Ajeet,Jain, Rajeev,Dubey, Devendra Kumar
experimental part, p. 3795 - 3797 (2012/09/21)
Mild and efficient esterification of alkylphosphonic acids using primary alcohols, iodine, imidazole and polymer-bound triphenylphosphine is developed.
Highly enantioselective hydrogenation of β-acyloxy and β-acylamino α,β-unsaturated phosphonates catalyzed by rhodium phosphane-phosphite complexes
Chavez, M. Angeles,Vargas, Sergio,Suarez, Andres,Ulvarez, Eleuterio,Pizzano, Antonio
experimental part, p. 2775 - 2794 (2011/12/21)
The enantioselective hydrogenation of β-(acyloxy)- and β-(acylamino)vinylphosphonates with rhodium catalysts based on chiral phosphane-phosphite ligands has been studied. In the case of the β-(acyloxy)vinylphosphonates, the reaction also produces an achiral phosphonate resulting from the elimination of the benzoate group. High ligand modularity has led to a highly chemo- and enantioselective catalyst for both types of substrates, which afford a good range of β-acyloxy- and β-acylaminophosphonates with enantioselectivities between 90 and 99% ee. Most interestingly, the configuration of the hydrogenation products indicates the same stereochemical sense for the reduction of both types of substrates, which is opposite to that observed before for α-(acyloxy) vinylphosphonates. This observation has been rationalized by assuming the formation of a β-alkyl intermediate during the catalytic cycle, which also explains the formation of the elimination product in the hydrogenation of the β-(acyloxy)-vinylphosphonates. Copyright
Highly enantioselective hydrogenation of enol ester phosphonates: A versatile procedure for the preparation of chiral β-hydroxyphosphonates
Vargas, Sergio,Suarez, Andres,Alvarez, Eleuterio,Pizzano, Antonio
supporting information; experimental part, p. 9856 - 9859 (2009/10/02)
A study was conducted to demonstrate a procedure for the preparation of chiral β-hydroxyphosphonates. The reaction sequence was investigated and the validity of the approach was demonstrated. The study also reported an olefin hydrogenation reaction, which gives access to a wide variety of chiral β-hydroxyphosphonates 2, with excellent levels of asymmetric induction, which can be converted into the corresponding alcohols. The application of phosphane-phosphite ligands 4 and 5 were investigated in diverse hydrogenation reactions. Unsaturated phosphonates 1 were chosen as substrates, in an effort to broaden the scope of these catalysts. Investigations were also initiated by the development of a convenient procedure for the synthesis of a set of olefins 1.
P-Toluenesulfonic acid-Celite as a reagent for synthesis of esters of alkylphosphonic acids under solvent-free conditions
Gupta, Arvind K.,Kumar, Rajesh,Dubey, Devendra K.,Kaushik
, p. 328 - 331 (2008/02/10)
The coupling reaction of alkylphosphonic acids and alcohols on the surface of p-toluenesulfonic acid-Celite under mild and solvent-free conditions gave the corresponding phosphonates in excellent yields. This method provides a useful rapid synthesis of phosphonates for use in the unambiguous identification of chemical warfare agents.
An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride
Sathe, Manisha,Gupta, Arvind K.,Kaushik
, p. 3107 - 3109 (2007/10/03)
Silica chloride is used as an effective heterogeneous catalyst for the rapid esterification of alkyl/aryl phosphonic/phosphoric acids to their corresponding alkyl/aryl phosphonates/phosphates under mild conditions with quantitative yields.
Surface-mediated solid phase reactions: A simple, efficient and base-free synthesis of phosphonates and phosphates on Al2O3
Acharya, Jyotiranjan,Shakya, Purushottam D.,Pardasani, Deepak,Palit, Meehir,Dubey, Devendra K.,Gupta, Arvind K.
, p. 194 - 196 (2007/10/03)
Al2O3-supported solvent free condensation of alkylphosphonic dichlorides with alcohols at room temperature yielded phosphorus esters in excellent yields.
