RSS-Feed abonnieren
DOI: 10.1055/s-2006-947323
One-Pot Wittig Reactions in Water and in the Presence of a Surfactant
Publikationsverlauf
Publikationsdatum:
04. Juli 2006 (online)
Abstract
α,β-Unsaturated esters were synthesized in open atmosphere via mild and efficient one-pot Wittig reactions performed in both water and sodium dodecyl sulfate (SDS)-water solution.
Key words
alkenes - esters - Wittig reaction - micelles
-
1a
Sinou D. Adv. Synth. Catal. 2002, 344: 221 -
1b
Lindstroem UM. Chem. Rev. 2002, 102: 2751 - 2
Maryanoff BE.Reitz AB. Chem. Rev. 1989, 89: 863 - 3
Broos R.Anteunis M. Synth. Commun. 1976, 6: 53 -
4a
Russel MG.Warren S. Tetrahedron Lett. 1998, 39: 7995 -
4b
Russel MG.Warren S. J. Chem. Soc., Perkin Trans. 1 2000, 505 - 5
Sieber F.Wentworth P.Toker JD.Wentworth AD.Metz WA.Reed NN.Janda KD. J. Org. Chem. 1999, 64: 5188 - 6
Villieras J.Rambaud M.Graff M. Tetrahedron Lett. 1985, 26: 53 - 7
Wu J.Zhang D.Wie S. Synth. Commun. 2005, 35: 1213 - 8
Dambacher J.Zhao W.El-Batta A.Anness R.Jiang C.Bergdahl M. Tetrahedron Lett. 2005, 46: 4473 - 9
Dwars T.Paetzold E.Oehme G. Angew. Chem. Int. Ed. 2005, 44: 7174 - 12
Zhao H.Cai MZ.Peng CY. Synth. Commun. 2002, 32: 3419 - 13
Barrett AGM.Cramp SM.Roberts RS.Zecri FJ. Org. Lett. 1999, 1: 579 -
14a
Concellon JM.Concellon C.Mejica C. J. Org. Chem. 2005, 70: 6111 -
14b
Suri CS.Marcischak CJ. Synth. Commun. 2005, 35: 379 - 15
Still WC.Kahn M.Mitra A. J. Org. Chem. 1978, 43: 2923
References and Notes
Phosphonium dodecylsulfate was isolated from a blank reaction performed as reported below in the absence of the base and of the electrophile: ethyl α-bromo acetate (0.5 mmol) was added, under stirring, to a solution of SDS (0.05 g) in H2O (0.5 mL), followed by the addition of tri-n-butylphosphine (0.5 mmol). The reaction mixture was poured in EtOAc (10 mL); Na2SO4 was added under stirring to remove H2O, filtered and washed with EtOAc (3 × 5 mL). The organic solvent was removed under reduced pressure. The residue was washed with n-hexane, dried, and dissolved in CDCl3: 1H NMR (CDCl3): δ = 0.86 (3 H, t, J = 7.0 Hz), 0.96 (9 H, t, J = 6.8 Hz), 1.20-1.23 (16 H, m), 1.31 (3 H, t, J = 6.8 Hz), 1.30-1.45 (2 H, m), 1.45-1.55 (12 H, m), 1.55-1.70 (2 H, m), 2.40-2.50 (6 H, m), 3.79 (2 H, d, J = 13.2 Hz), 4.01 (2 H, t, J = 7.5 Hz), 4.20 (2 H, q, J = 6.8 Hz).
11All products were isolated by flash chromatography. Their purity, structure and stereoisomeric ratios (when E/Z mixtures were obtained) were determined by 1H NMR analysis, in comparison with the literature data.