1067-90-9Relevant articles and documents
A study on the michael addition of dialkylphosphites to methylvinylketone
Keglevich, Gyoergy,Sipos, Melinda,Takacs, Daniella,Greiner, Istvan
, p. 226 - 229 (2007)
The addition of dialkylphosphites to methylvinylketone giving dialkyl-3-oxobutyiphosphonates was studied applying different reagents, such as NaOR/ROH, NaOH/H2O under PTC, DBU, and R3Al (R = Me, Et) under different conditions to find
Zinc-Mediated Chain Extension of β-Keto Phosphonates
Verbicky, Christopher A.,Zercher, Charles K.
, p. 5615 - 5622 (2000)
A variety of β-keto phosphonates can be converted to γ-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of α-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of β-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of β-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for γ-keto phosphonate formation.
Metallo-phosphorylation of olefins: Reaction of diethyl chlorophosphate with Zirconocene-ethylene complex
Xi,Ma,Li
, p. 2554 - 2555 (2001)
Zirconocene-ethylene complex Cp2Zr (CH2 = CH2) reacted with chlorophosphate to form zircono-ethylphosphonate, which could be converted into various functionalized ethylphosphonates.
1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): Three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems
Simoni, Daniele,Rondanin, Riccardo,Morini, Massimo,Baruchello, Riccardo,Invidiata, Francesco Paolo
, p. 1607 - 1610 (2000)
The 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its 7-methyl derivative (MTBD) have been proven to be of great synthetic utility as catalysts in the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to a variety of carbonyl compounds. The catalysts were in many cases superior to the parent tetramethylguanidine (TMG). In general the reaction proceeds in a few minutes at 0°C. The polymer-supported-TBD (P- TBD) was also proven to be an efficient promoter of the above cited nucleophilic additions. (C) 2000 Elsevier Science Ltd.
Cyclopropanation of 1,2-dibromoethylphosphonate: A synthesis of β-aminocyclopropylphosphonic acid and derivatives
Rabasso, Nicolas,Fadel, Antoine
, p. 6068 - 6071 (2014)
Diethyl (1,2-dibromoethyl)phosphonate was found to undergo cyclopropanation with nitromethane in good yield. The resulting trans β-nitrocyclopropylphosphonate was converted to the trans N-protected aminocyclopropylphosphonate through a reduction-protection sequence. Subsequent hydrolysis gave the free β-aminocyclopropylphosphonic acid without any formation of ring-opening byproduct. Cyclopropanation of 1,2-dibromoethylphosphonates with nitroalkanes and their reduction are also discussed.
N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts
Hans, Morgan,Delaude, Lionel,Rodriguez, Jean,Coquerel, Yoann
, p. 2758 - 2764 (2014/04/17)
N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.
A green procedure for the regio- and chemoselective hydrophosphonylation of unsaturated systems using CaO under solventless conditions
Martinez-Castro, Elisa,Lopez, Oscar,Maya, Ines,Fernandez-Bolanos, Jose G.,Petrini, Marino
supporting information; experimental part, p. 1171 - 1174 (2010/10/18)
Diethyl phosphite and diphenylphosphine add to a series of unsaturated derivatives using environmentally-friendly calcium oxide as a basic promoter under solventless conditions at room temperature. The corresponding adducts are obtained in a totally regio
NOVL AND EFFICIENT SYNTHESIS OF URACIL PHOSPHONATE DERIVATIVES VIA PENTACOVALENT OXAPHOSPHOLENES
McClure, Cynthia K.,Grote, Christopher W.,Rheingold, Arnold L.
, p. 983 - 986 (2007/10/02)
2,2,2-Triethoxy-1,2λ5-oxaphospholene, 1, reacts under mild, neutral conditions with aryl isocyanates to produce the phosphonate-containing pyrimidinedione derivatives 2 and 3.X-ray structure determination of 3 confirmed its structure.Keywords:
Methylenomycin B: New Syntheses Based on β- and γ-Keto Phosphonates and γ-Keto Phosphine Oxides
Mikolajczyk, Marian,Zatorski, Andrzej
, p. 1217 - 1223 (2007/10/02)
Methylenomycin B has been synthesized from diethyl 2-oxobutanephosphonate (4) in three steps in 39 percent overall yield.Starting from diethyl 3-oxobutanephosphonate (10) and diphenyl(3-oxobutyl)phosphine oxide (13), methylenomycin B has been obtained in 34 percent and 27 percent overall yield, respectively.A characteristic feature of these syntheses of methylenomycin B is that the exo-methylene function is introduced via the Horner-Wittig reaction of formaldehyde (36 percent aqueous solution) with the corresponding α-phosphorylcyclopentenones 6 and 20.The latter were obtained from phosphorylated 1,4-diketones by intramolecular base-catalyzed cyclization.A brief discussion of some mechanistic aspects of the Conant reaction is also given.
