Synthesis and Variable Temperature 1 H and 31 P NMR Study of Phosphorus Ylides derived from reaction of NH-acids,triarylphosphine and acetylenic esters
Free accessResearch articleFirst published online June, 2007
Synthesis and Variable Temperature 1 H and 31 P NMR Study of Phosphorus Ylides derived from reaction of NH-acids,triarylphosphine and acetylenic esters
A one-step synthesis of sterically congested phosphorus ylides in moderate to good yields by the reaction of dialkyl acetylenedicarboxylates, NH-acids and triarylphosphines are reported. Characterisation of the obtained compounds was performed by IR, 1H, 31P, 13C NMR, elemental analysis and mass spectroscopy. NMR spectra showed that some of these compounds (in CDCl3 as solvent) contained two rotamers with unequal populations that equilibrate rapidly at higher temperatures.
PukeC., ErkerG., AustN.C., WurthweinE.U., and FrohichR., J. Am. Chem. Soc.1998, 120, 4863.
3.
KolodiazhnyiO.I., Russ. Chem. Rev.1997, 66, 225.
4.
CobridgeD.E.C., Phosphorus an Outline of Chemistry, Biochemistry and Uses, 5th edn, Elsevier, Amsterdam, 1995.
5.
HudsonH.R., Primary, Secondary and Tertiary Phosphines, Polyphosphines and Heterocyclic Organophosphorus (III) Compounds; in the Chemistry of Organophosphorus Compounds, Vol. 1. HartleyF.R., (ed.) Wiley: New York, 1990, p. 386.
6.
EngelR., Synthesis of Carbon–Phosphorus Bonds, CRC: Boca Raton, FL, 1988.
7.
CadoganJ.I.G., Organophosphorus Reagents in Organic SynthesisAcademic: New York, 1979.
8.
MaryanoffB.E., and ReitzA.B., Chem. Rev.1989, 89, 863.
9.
SabouncheiS.J., and KaramiK., Phosphorus, Sulfur, and Silicon, 2004, 179, 2029.
10.
SabouncheiS.J., DadrassA.R., and JodaianV., J. Chem. Res., 2007, 94.
11.
ShaabaniA., safaeiH.R., HemyariK., and MoghimiA., J. Chem. Res., 2001, 192.
12.
RamazaniA., and BodaghiA., Tetrahedron Lett., 2000, 41, 567.
