16524-41-7Relevant articles and documents
Cyclic analogues of the Hendrickson 'POP' reagent
Elson, Kathryn E.,Jenkins, Ian D.,Loughlin, Wendy A.
, p. 371 - 376 (2004)
The Hendrickson reagent, triphenylphosphonium anhydride trifluoromethanesulfonate, 'POP' 1, is a powerful dehydrating agent. Five-, six-, and seven-membered cyclic analogues of the 'POP' reagent 2-4 have been prepared and their use for ester and amide synthesis investigated. A kinetic comparison of the cyclic analogues 2-4 revealed that a considerable increase in the rate of esterification could be achieved when the five-membered ring analogue 2 was used, presumably due to the ease of formation of the putative phosphorane intermediate. The rate of ester formation from a primary alcohol using the Hendrickson reagent 1 was shown to be significantly faster when non-polar solvents were employed.
Intramolecular stabilization of the phosphine radical cation by the second phosphorus atom during the photooxidation of diphosphines:31P NMR spectroscopic analysis
Yasui, Shinro,Yamazaki, Shoko
, p. 422 - 424 (2015)
Diphosphines, Ph2P(CH2)nPPh2 1 (n = 1, 2, 3, 4, and 6), were photolyzed by a xenon lamp in air. The 31P NMR spectroscopic analysis of the reaction showed that 1 is oxidized, according to first-order kinetics, to the monoxide, which is further oxidized to the dioxide. The dependence of the rate constants for the first oxidation on the chain-length n in 1 is interpreted in terms of the orientation of the p-orbitals on the two phosphorus atoms in the intermediate, the diphosphine radical cation.
Selective synthesis and stabilization of peroxides: Via phosphine oxides
Arp, Fabian F.,Ahn, Shin Hye,Bhuvanesh, Nattamai,Blümel, Janet
, p. 17174 - 17181 (2019)
Reaction of bis(dicyclohexylphosphino)ethane dioxide with hydrogen peroxide leads to an extended crystalline network based on the formation of hydrogen bonds with the PO groups of the diphosphine dioxide. The structural motif of the network is characterized by X-ray diffraction. A new selective synthesis for an industrially important MEKPO (methyl ethyl ketone peroxide) dimer is described. The dimer is created by reaction of dppe dioxide (bis(diphenylphosphino)ethane dioxide) with butanone and hydrogen peroxide. This peroxide is stabilized by forming strong hydrogen bonds to the phosphine oxide groups within an extended network, which has been characterized by single crystal X-ray diffraction. Reaction of acetylacetone with hydrogen peroxide, irrespective of the presence of phosphine oxide, leads to the stereoselective formation of two dioxolanes. Both cyclic peroxides have been obtained in crystalline forms suitable for single crystal X-ray diffractions.
Compound containing bis-diphenyl phosphinic oxygen structure and preparation method thereof
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Paragraph 0039-0040, (2021/04/21)
The invention discloses a compound containing a bis-diphenyl phosphinic oxygen structure and a preparation method of the compound, and belongs to the technical field of organic synthesis. In a polar solvent, diphenyl phosphorus chloride or diphenyl phosph
Dearylation of arylphosphine oxides using a sodium hydride-iodide composite
Tejo, Ciputra,Pang, Jia Hao,Ong, Derek Yiren,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 1782 - 1785 (2018/02/21)
A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.
