67293-73-6Relevant academic research and scientific papers
Synthesis of organophosphates starting from α-hydroxyphosphonates
Kiss, Nóra Z.,Rádai, Zita,Szabó, Réka,Aichi, Youness,Laasri, Laila,Sebti, Said
, p. 370 - 371 (2019)
α-Hydroxyphosphonates were successfully converted to the corresponding phosphates applying the phospha-Brook rearrangement under phase transfer catalytic conditions. Among several possible catalysts tested, K2CO3, Cs2CO3, as well as modified Moroccan phosphates were found to be suitable.
α-Hydroxyphosphonates as intermediates in the Kabachnik–fields reaction: New proof of their reversible formation
Keglevich, Gy?rgy,Rádai, Zita
, (2020/05/18)
The rearrangement of dimethyl α-hydroxybenzylphosphonate to the corresponding benzylphosphate in the presence of an alkali carbonate in acetone under phase transfer catalytic conditions was accompanied by the formation of dimethyl α–hydroxyisopropylphosph
An efficient method for phosphorylation of alcohols: Preparation of porphyrin-derived phosphates
Pisarek, Sabina,Bednarski, Hubert,Gryko, Dorota
, p. 2667 - 2671,5 (2012/12/12)
An effective method for the phosphorylation of phenols and various alcohols including porphyrins bearing hydroxyl groups was developed. The reaction of 6,7-bis(3-hydroxypropyl)-1,3,5,8-tetramethyl-2,4-divinylporphyrin with dialkyl chlorophosphate in the presence of DABCO as both a catalyst and a proton scavenger gave the desired phosphate in 97% yield.
An efficient method for phosphorylation of alcohols: Preparation of porphyrin-derived phosphates
Pisarek, Sabina,Bednarski, Hubert,Gryko, Dorota
, p. 2667 - 2671 (2013/01/15)
An effective method for the phosphorylation of phenols and various alcohols including porphyrins bearing hydroxyl groups was developed. The reaction of 6,7-bis(3-hydroxypropyl)-1,3,5,8-tetramethyl-2,4-divinylporphyrin with dialkyl chlorophosphate in the presence of DABCO as both a catalyst and a proton scavenger gave the desired phosphate in 97% yield. Georg Thieme Verlag KG Stuttgart · New York.
Transesterification of trialkyl phosphates from alkyl bromides
Lherbet, Christian,Castonguay, Roselyne,Keillor, Jeffrey W.
, p. 3565 - 3567 (2007/10/03)
The treatment of trialkyl phosphate with different alkyl bromides provides facile access to mixed phosphate esters. The presence of substoichiometric amounts of lithium bromide was found to be critical to this transesterification process, supporting a mechanism involving initial generation of phosphate anion, followed by its nucleophilic attack on alkyl bromide.
Enantioselective Deprotonation of Benzyl Phosphates by Homochiral Lithium Amide Bases - Configurational Stability of Benzyl Carbanions with a Dialkoxyphosphoryloxy Substituent and Their Rearrangement to Optically Active α-Hydroxy Phosphonates
Hammerschmidt, Friedrich,Hanninger, Achim
, p. 823 - 830 (2007/10/02)
Benzyl dialkyl phosphates are deprotonated enantioselectively by homochiral lithium amides of isopropyl(1-phenylethyl)amine or bis(1-phenylethyl)amine.The short-lived benzylic carbanions formed are virtually configurationally stable relative to the rearrangement to optically active phenylhydroxymethylphosphonates.The enantiomeric excesses are up to 50percent.The pro-(S) hydrogen is removed by amides having (S) configuration.Homochiral diethyl (S)-phenylmethyl phosphate is deprotonated by both LDA and n-BuLi with a high primary kinetic isotope effect (kH/D ca. 50) and isomerizes to the corresponding α-hydroxy phosphonate with an enantiomeric excess of up to 85percent. - Keywords: Phosphate-phosphonate rearrangement / Carbanions, benzylic, configurational stability of / Phosphonates / Lithium amides, homochiral
Solvation and metal ion effects on structure and reactivity of phosphoryl compounds. Part 4. Dealkylation of phosphate esters by thiophenoxide ion in methanol
Mentz,Modro,Modro
, p. 1933 - 1960 (2007/10/02)
Second-order rate constants for the demethylation of three phosphate esters by thiophenoxide salts, PhS-M+ (M+ = Me4N+, K+, Na+Li+) in methanol-d4 at 25°C have been measured. In contrast to the demethylation by iodide salts, metallic counterions do not exhibit any catalytic effects on the demethylation rate. The absence of the catalysis indicates that the salts react exclusively as ion pairs, in which an alkali metal ion is not available for the interactions with the phosphoryl group in the transition state.
CATALYTIC EFFECT OF CESIUM FLUORIDE FOR ALKYLATION OF PHOSPHORIC ACIDS
Takaku, Hiroshi,Kamaike, Kazuo,Mori, Hisashi,Ishido, Yoshiharu
, p. 2157 - 2159 (2007/10/02)
The phosphoric acids were smoothly alkylated with alkyl halides in the presence of cesium fluoride.KEYWORDS - phosphorylation; phosphotriester; cesium fluoride; alkylation
