Inverse phase transfer catalysis. III.- Optimization of the epoxidation reaction of α,β-unsaturated ketones by hydrogen peroxide

Tetrahedron

Volumn 55, Issue 19, 1999, Pages 6147-6152

  Boyer, Bernard ^a   Hambardzoumian, Araik ^a   Roque, Jean Pierre ^a   Beylerian, Norair ^b  

^a UNIV MONTPELLIER   (France)

^b YEREVAN STATE UNIVERSITY   (Armenia)

Author keywords

Epoxidation; Hydrogen peroxide; Phase transfer catalysis; Surfactant

Indexed keywords

HYDROGEN PEROXIDE; KETONE; SURFACTANT;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); PH; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033532189     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00270-7     Document Type: Article

References (23)

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8. 1. This result proves really that the catalytic effect cannot be explained by a normal Phase Transfer Catalysis mechanism in which the anionic reactant is transferred in the organic phase by the surfactant.
9. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
10. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
11. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
12. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
13. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
14. For reviews of epoxidation reactions using chalcone as model, see: Sharifi, A.; Bolourtchian, M.; Mohsenzadeh, F. J. Chem. Res. 1998, 668; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Lygo, B.; Wainwright, P.G. Tetrahedron Lett. 1998 ,39, 1599; Cappi, M.W.; Chen, W.P.; Flood, R.W.; Liao, Y.M.; Roberts, S.M.; Skidmore, J.; Smith, J.A.; Williamson, N.M. Chem. Commun. 1998, 1159; Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321; Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353; Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563; Bentley, P.A.; Cappi, M.W.; Flood, R.W.; Roberts, S.M.; Smith, J.A. Tetrahedron Lett. 1998, 39, 9297.
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17. The measured pH is actually the pH of the aqueous phase before iniating the reaction. Since the reaction mixture becomes heterogeneous during the reaction, it is not possible to realize the measure of the pH medium.
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