6224-95-9Relevant academic research and scientific papers
The Diels-Alder reaction of diphenyl(1,2-propadienyl)phosphine oxide and diphenyl(1-propynyl)phosphine oxide with cyclopentadiene
Maffei, Michel
, p. 1323 - 1328 (2004)
The Diels-Alder reaction of diphenyl(1,2-propadienyl)phosphine oxide 1 and diphenyl(1-propynyl)phosphine oxide 2 with cyclopentadiene is reported. 1 reacts smoothly at room temperature in the presence of one equivalent of aluminum trichloride to give the corresponding adducts endo 3a and exo 3b (90:10 ratio) whose structure was attributed on the basis of their 13C NMR spectra, whereas 2 is a poor dienophile, affording the corresponding adduct in low yield even under harsh conditions.
Synthesis of diarylenynes by olefination of 1-arylpropyne with arylaldehyde and their optical properties
Shinohara, Kenta,Nishida, Takanori,Wada, Ryosuke,Peng, Lifen,Minoda, Yuju,Orita, Akihiro,Otera, Junzo
, p. 4427 - 4434 (2016/07/06)
A new synthetic protocol of 1-arylpropyne was developed by taking advantage of 1-(diphenylphosphoryl)propyne as propyne equivalent in Sonogashira coupling: consecutive subjection of phosphorylpropyne to t-BuOK and to aryl halides in the presence of Pd and Cu catalysts afforded the corresponding 1-arylpropynes. The following olefination of the 1-arylpropyne with aldehyde provided the corresponding diarylenyne. When the enynes thus obtained were irradiated with UV light, they showed strong emission in organic solvents and in the solid states. In solution, Ph2N-substituted enynes exhibited remarkable solvatofluorochromism, and Lippert–Mataga plot analysis demonstrated that they undergo the larger polarization in the excited states than in the ground states.
Stereoselective inverse conjugate addition of nitrogen and carbon nucleophiles to allenyl phosphine oxide. Synthesis of α,β-unsaturated phosphine oxides
De Los Santos, Jesus M.,Ochoa, Zelai,Palacios, Francisco
experimental part, p. 54 - 62 (2012/03/10)
The reactivity of new three carbon synthon, generated in situ from the reaction of electrondeficient allenes with an appropriate phosphine as the catalyst, toward pronucleophilic reagents is described. Triphenylphosphine- catalyzed reaction of allenes derived from phosphine oxides with nitrogen- or carbonucleophiles gave the γ-addition product as a mixture of cis and trans isomers. ARKAT-USA, Inc.
Zn(OTf)2 catalyzed addition-cyclization reaction of allenylphosphine oxides with propargyl alcohol-unexpected formation of 2,5-dimethylenetetrahydrofurans and 2-substituted furans
Srinivas, Venu,Sajna,Kumara Swamy
body text, p. 5323 - 5326 (2011/10/19)
A novel synthesis of 2,5-dimethylenetetrahydrofurans, 2-substituted furans and a β,ω-diketophosphonate in good to excellent yields has been achieved by the reaction of allenylphosphine oxides/allenylphosphonate with propargyl alcohol using zinc triflate/t
Efficient palladium-catalyzed double arylation of phosphonoalkynes and diarylalkynes in water: Use of a dinuclear palladium(I) catalyst
Sajna,Srinivas, Venu,Kumara Swamy
scheme or table, p. 3069 - 3081 (2011/02/22)
A novel use of the dinuclear palladium(I) catalyst [(OCH 2CMe2CH2O)P-S-Pd(PPh3)]2 in aqueous medium for the double arylation of phosphonoalkynes as well as diarylalkynes is reported. This double arylation requires both the iodoarene and arylboronic acid along with the catalyst. The structures of some key products have been proven by X-ray crystallography. Copyright
Phosphine-catalyzed synthesis of unsymmetrical 1,3-bis- and trisphosphorus ligands
Lin, Yi,Bernardi, Dan,Doris, Eric,Taran, Frédéric
experimental part, p. 1466 - 1470 (2011/04/15)
Phosphine-catalyzed umpolung γ-additions of phosphorus pronucleophiles on alkynes bearing phosphinoyl (P=O) or phosphinothioyl (P=S) moieties have been explored. The reaction leads to bis- or trisphosphorus subunits that can be useful for the preparation of chelating ligands. Georg Thieme Verlag Stuttgart.
Quaternary ammonium salts as alkylating agents in the synthesis of tertiary phosphine oxides
Zalinyan, S. A.,Khachatryan, R. A.,Indzhikyan, M. H.
, p. 388 - 390 (2007/10/03)
A procedure was developed for the synthesis of tertiary phosphine oxides by alkylation of secondary phosphine oxides with quaternary ammonium salts.
