5137-70-2Relevant academic research and scientific papers
Synthesis of Long-Chain n-Alkylphosphonic Acids by Phosphonylation of Alkyl Bromides with Red Phosphorus and Superbase under Micellar/Phase Transfer Catalysis
Kuimov, Vladimir A.,Malysheva, Svetlana F.,Belogorlova, Natalia A.,Albanov, Alexander I.,Gusarova, Nina K.,Trofimov, Boris A.
supporting information, p. 1596 - 1602 (2021/03/03)
Long-chain n-Alkylphosphonic acids, AlkP(O)(OH)2, are synthesized in up to 91 % yield (mostly 40–60 %) by straightforward phosphonylation of alkyl bromides (AlkBr, Alk=C4–C18) with red phosphorus (Pn) in the multiphase KOH/H2O/toluene system in the presence of 2–10 mol % of cetyltrimethylammonium bromide (CTAB), acting as a micellar/phase transfer catalyst and as a generator/transporter of superbasic hydroxide anions, the intermediate potassium phosphinates being in situ oxidized/neutralized by nitric acid. The key steps of the phosphonylation mechanism are the P?P bond cleavage of Pn polymeric molecules by superbasic ?OH anions, dissolved in the CTAB micelles, and phase transfer of polyphosphide anions to the organic phase and their alkylation with AlkBr.
Friedl?nder synthesis of poly-substituted quinolines in the presence of dodecylphosphonic acid (DPA) as a highly efficient, recyclable and novel catalyst in aqueous media and solvent-free conditions
Ghassamipour,Sardarian
body text, p. 514 - 519 (2009/04/14)
Poly-substituted quinolines were synthesized in the presence of a catalytic amount of dodecylphosphonic acid (DPA) in aqueous media and solvent- free conditions. The reactions proceed very well under relatively mild conditions, and DPA can be recycled.
Microwave michaelis-becker synthesis of diethyl phosphonates, tetraethyl diphosphonates, and their total or partial dealkylation
Meziane, Dalila,Hardouin, Julie,Elias, Abdelhamid,Guenin, Erwann,Lecouvey, Marc
experimental part, p. 369 - 377 (2010/07/16)
Diethyl phosphonates and tetraethyl alkyldiphosphonates were efficiently and rapidly prepared via the Michaelis-Becker reaction, under microwave irradiation. These compounds were then hydrolyzed to phosphonic and diphosphonic acids or selectively monodealkylated to give monoesters of phosphonic acids and symmetrical diethyl esters of diphosphonic acids. These reactions were also achieved rapidly in satisfactory yields with microwave methodology. This methodology was applied with success to the functionalization of a polymer resin.
Facile manufacture and storage of poly(methylhydrogenosiloxane)s
Yactine, Bassem,Ganachaud, Francois,Senhaji, Omar,Boutevin, Bernard
, p. 2230 - 2236 (2007/10/03)
This paper describes the ring-opening polymerization of 2,4,6,8-tetramethylcyclotetrasiloxane (D4H) in miniemulsion, using mono- and diphosphonic acid surfactants. In the simplest formulation conditions, polymerization proceeds in less than 15 min to generate linear poly(methylhydrogenosiloxane) (PMHS) of large molar masses (typical number-average of 25 kg/mol), of low polydispersities (around 2), and in good yields (up to 94%), Molar masses can be tuned at will since for similar conversions but increasing times, Mn varies between 10 and 30 kg/mol. After 4 h reaction, some redistribution reactions start to proceed, responsible for PMHS chains switching into macrocycles. It was shown that rising the pH to stop the polymerization and breaking the emulsion with excess of alun salt induced hydrolysis/condensation reactions, which rapidly convert the polymer chains into an unwished macrogel. Rather, extracting the polymer by simple centrifugation and using the diacid surfactant induce a physical gelling that very efficiently suppresses side reactions, as shown by minor evolution of the molar mass distribution for 10 months.
Cannabinoid CB1 receptor chemical affinity probes: Methods suitable for preparation of isopropyl [11,12-3H]dodecylfluorophosphonate and [11,12-3H]dodecanesulfonyl fluoride
Segall, Yoffi,Quistad, Gary B.,Casida, John E.
, p. 2151 - 2159 (2007/10/03)
Preparations of isopropyl dodec-11-enylfluorophosphonate and dodec-11-enesulfonyl fluoride are described along with conditions for their reduction with hydrogen (or potentially tritium) gas to the 1-dodecane derivatives as candidate high-potency (IC50 0.5-7 nM) chemical affinity probes for the mouse brain cannabinoid CB1 receptor and fatty acid amide hydrolase.
Synthesis and structural study of long-chain hydrocarbon alkylphosphonic acids
Gaboyard,Hervaud,Boutevin
, p. 877 - 891 (2007/10/03)
Long-chain dialkyl alkylphosphonates were synthesized by radical addition of dialkyl hydrogenphosphonates onto alkenes in presence of di(t-butyl) peroxide. This synthetic route leads to high yields between 94 and 97%. We performed chemical modifications of these phosphonates in order to obtain acidic derivatives. The structure of these compounds was characterized by NMR analyses and mass spectroscopy. We also studied their thermal behaviour and various crystalline phases were put in evidence by differential scanning calorimetry and optical microscopy. The thermal stability of these compounds was compared by thermogravimetric analyses.
