54664-07-2Relevant academic research and scientific papers
2-Phenoxyethyldiphenylphosphine oxide as an equivalent of diphenylvinylphosphine oxide in nucleophilic additions
Bondarenko, Natalia A.,Tcarkova, Kseniia V.,Belus', Svetlana K.,Artyushin, Oleg I.
, p. 902 - 910 (2021/06/25)
A facile method for the synthesis of β-functionalized ethyldiphenylphosphine oxides is developed based on readily available 2-phenoxyethyldiphenylphosphine oxide used as an equivalent of diphenylvinylphosphine oxide in the reactions of addition of different PH- and NH-nucleophiles in DMSO in the presence of KOH. The transformations of labile phosphine oxides of a general formula Ph2P(O)CH2CH2OR, where R = Ph, H, or Ph2P(O)CH = CH2, in aq.KOH/DMSO and solid KOH/DMSO systems are explored in the absence of nucleophilic reagents.
New method for the syntheses of 2-aminoethyldiphenylphosphine oxides under the phase transfer conditions using cesium carbonate
Artyushin, Oleg I.,Belus', Svetlana K.,Bondarenko, Natalia A.,Tcarkova, Kseniia V.
, (2021/12/02)
A simple one-pot method for the synthesis of 2-aminoethyldiphenylphosphine oxides is developed based on readily available diphenyl(2-phenoxyethyl)phosphine oxide and amines of different types under phase transfer catalysis conditions using anhydrous cesium carbonate as a base in acetonitrile or DMSO.
A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-michael reaction in water
Matveeva, Ekaterina V.,Shipov, Anatoly E.,Odinets, Irina L.
scheme or table, p. 698 - 706 (2011/06/23)
Application of water as a solvent (without any cosolvent) promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with a wide range of N-nucleophiles. The solubility of the starting phosphorus substrate in water does not play a crucial role in the reaction course, decreasing to some extent the reaction rate. The reaction can be performed either at room temperature or under reflux to afford the corresponding β-aminophosphonates and β-aminophosphine oxides in excellent yields and of high purity via a simple freeze-drying isolation procedure. Application of basic catalysts makes possible the addition of weak nucleophiles such as a-amino acids and their phosphorus analogues; that is, a-aminophosphonic acids. The aqueous aza-Michael reaction allowed us to easily perform double phosphorylation of primary amines including polyamines using a reactant ratio (phosphorus substrate: amine) of 2:1. Copyright Taylor & Francis Group, LLC.
A practical and efficient green synthesis of β-aminophosphoryl compounds via the aza-Michael reaction in water
Matveeva, Ekaterina V.,Petrovskii, Pavel V.,Klemenkova, Zinaida S.,Bondarenko, Natalya A.,Odinets, Irina L.
experimental part, p. 964 - 970 (2011/11/05)
Biphasic systems room temperature imidazolium ionic liquid (RTIL)/water or water as a solvent significantly accelerate the addition of amines to vinylphosphoryl compounds hence opening green and effective synthesis of β-aminophosphoryl compounds in excellent yields over short reaction times. The application of water, being the cheapest and most non-toxic solvent, without any catalyst or co-solvent, is more advantageous as it provides a simple isolation procedure for products having high purity (> 95% according to the NMR data) via simple freeze-drying and does not require extraction with organic solvents. The solubility of the starting phosphorus substrate in water does not play crucial role in the reaction as it was demonstrated using water insoluble diphenylvinylphosphine oxide. In contrast to typical procedures, using a reactant ratio (vinylphosphoryl compound: amine) of 2:1 readily resulted in double phosphorylation of primary amines, including polyamines, in water.
REGIO- AND STEREOSPECIFIC SYNTHESIS OF ALLYLIC TERTIARY AMINES
Cavalla, David,Warren, Stuart
, p. 4505 - 4508 (2007/10/02)
E and Z allylic amines have been synthesised by stereospecific elimination of Ph2PO2- from pure diastereoisomers (3) and (4).
