54664-06-1Relevant articles and documents
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.
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.
Horner-Wittig Reactions of β-Aminoalkyl- and β-N-Acylaminoalkyldiphenylphosphine Oxides: Synthesis of N-Allyl Amines and Amides and 5-Diphenylphosphinoyl-2-phenyl-5,6-dihydro-4H-1,3-oxazines
Cavalla, David,Cruse, William B.,Warren, Stuart
, p. 1883 - 1898 (2007/10/02)
Lithium derivatives of β-diphenylphosphinoyl-alkyl amines and dilithium derivatives of the corresponding amides combine with aldehydes or ketones in the Horner-Wittig reaction.Separation of the diastereoisomeric intermediates leads to single positional and geometrical isomers of N-allyl amines and amides.Attempted rearrangement of the same intermediates in acid solution gives dihydro-oxazines or, in one cases, a γ-N-acylaminoallyl diphenylphosphine oxide.
