- 2-Phenoxyethyldiphenylphosphine oxide as an equivalent of diphenylvinylphosphine oxide in nucleophilic additions
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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.
- Bondarenko, Natalia A.,Tcarkova, Kseniia V.,Belus', Svetlana K.,Artyushin, Oleg I.
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p. 902 - 910
(2021/06/25)
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- Reduction of functionalized tertiary phosphine oxides with BH3
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A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphine-boranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O···B complexation directed by proximal aα- or β-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.
- Sowa, Sylwia,Stankevi?, Marek,Szmigielska, Anna,Ma?uszyńska, Hanna,Kozio?, Anna E.,Pietrusiewicz, K. Micha?
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p. 1672 - 1688
(2015/02/19)
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- Ruthenium-catalyzed regio- and enantioselective allylic substitution with water: Direct synthesis of chiral allylic alcohols
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Less is more: A new route to access chiral allylic alcohols through the regio- and enantioselective substitution of monosubstituted allylic chlorides with water has been developed. The reaction is catalyzed effectively by planar-chiral cyclopentadienyl ruthenium complexes (see scheme). Copyright
- Kanbayashi, Naoya,Onitsuka, Kiyotaka
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supporting information; experimental part
p. 5197 - 5199
(2011/06/26)
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- Regio- and stereospecific cleavage of stannyloxiranes with lithium diphenylphosphide
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Unsubstituted or C-substituted stannyloxiranes reacted stereospecifically with lithium diphenylphosphide to give either β-hydroxyphosphane oxides resulting from α-opening or β-phosphanyl ketones by β-opening. Furthermore, the reactivities of distannyloxir
- Gonzalez-Nogal, Ana M.,Cuadrado, Purification,Sarmentero, M. Angeles
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scheme or table
p. 850 - 859
(2009/07/17)
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- ALKALINE HYDROLYSIS OF β AND γ-FUNCTIONAL PHOSPHONIUM SALTS
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A model study of alkaline hydrolysis of β- and γ-heterosubstituted phosphonium salts has been made and used as a synthetic method to obtain diphosphine dioxides affording additional coordination sites in an alkyl chain linked to phosphorus.After synthesis of the corresponding salts, anomalous fragmentations, such as inversion in cleavage selectivity or participation of the reaction solvent, have been pointed out in alkaline hydrolysis of β-functional phosphonium salts.A mechanism is suggested to account for the presence of all compounds detected.In the case of γ-functional phosphonium salts, the alkaline hydrolysis leads only to predicted compounds corresponding to the usual selective cleavage of one phenyl group.The results observed have been used to synthesize symmetric and asymmetric diphosphine dioxides with ether substituted side chains. - Key words: Phosphonium salt, phosphine oxide, diphosphine dioxides, alkaline hydrolysis, cleavage, mechanism.
- Cristau, Henri-Jean,Mouchet, Patrick
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p. 135 - 144
(2007/10/03)
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- Process for the preparation of bisphosphine dioxides
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A process is disclosed for the preparation of 1,2-bis-phosphine oxides by reacting at least one of certain phosphine oxides with certain oxirane compounds in an aprotic solvent and in the presence of a basic compound.
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