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Original Articles

RAPID AND EFFICIENT PHOSPHONATION OF ARYL HALIDES CATALYSED BY PALLADIUM UNDER MICROWAVES IRRADIATION

, &
Pages 59-63 | Received 14 May 1997, Published online: 24 Sep 2006

References

  • Mingos , D. M. P. and Baghurst , D. R. 1991 . Chem. Soc. Rev. , 20 : 1 ;A. G. Whittaker and D. M. P. Mingos, J. Microw Pow. Electr. Energ., 30, 27(1995; S. Caddick, Tetrahedron, 51, 10403 (1995).
  • Adamek , F. and Hajek , M. 1992 . Tetrahedron Lett. , 33 : 2039 ; E. M. Gordon, D. C. Gaba, K. A. Jebber and D. M. Zacharias, Organometallics, 12, 5020 (1993); M. Larhed and A. Hallberg, J. Org. Chem., 61, 9582 (1996).
  • We used a Savilex autoclave and a commercial microwave oven Toshiba ER 8930.
  • Schull , T. L. , Fettinger , J. C. and Knight , D. A. 1995 . J. Chem. Soc. Chem. Commun. , : 1487 ; S. Lelièvre, F. Mercier and F. Mathey, J. Org. Chem., 61, 3531(1996.
  • Jaffrès , P. A. 1996 . Thèse de Doctorat de Chimie, Université de Caen, France(.
  • Bunnett , J. F. and Weisis , R. H. 1978 . Org. Synth. , 58 : 134 ; J. J. Bulot, E. E. Aboujaoude, N. Collignon and P. Savignac, Phosphorus and Sulfur, 21, 197 (1984).
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  • Roffia , P. , Conti , F. and Gregori , G. 1971 . Chem. Ind. (Milan , 53 : 361
  • Villemin , D. and Endo , S. 1985 . J. Organometal. Chem. , 283 C10(.
  • Carpentier , J. F. , Pamart , L. , Maciewjski , L. , Casttanet , Y. , Brocard , J. and Mortreux , A. 1996 . Tetrahedron Lett. , 37 : 167 . J. F. Carpentier, F. Pettit, A. Mortreux, V. Dufaud, J. M. Basset and J. Thivolle-Cazat, J. Mol. Cat., 81, 1 (1993).
  • 1H NMR spectra of new products. 2k: 1,33 (d; 3JHH = 7.1 Hz; CH3CH2O; 6H); 2.15 (s; CO-CH3; 3H); 4.10 (m; CH3CH2O; 4H); 5.44 (s; -CH2-O-; 2H); 7.4–7.7 (m; 3H); 7.9 (dd; 3JHH = 7.6 Hz; 3JHP = 14.3 Hz; H6; 1H); 21: 1.33 (d; 3JHH = 7.1 Hz; CH3CH2O; 6H); 3.46 (s; O-CH3; 3H); 4.10 (m; CH3CH2O; 4H); 4.78 (s; -CH2-O-; 2H); 7.36 (dt; 3JHH = 3JHH = 7.0 Hz; 4JHP = 2.2 Hz; H4; 1H); 7.5–7.7 (m; H3 et H5; 2H); 7.92 (ddd; 3JHH = 7.6 HZ; 3JHP = 14.3 HZ; 4JHH = 2.2 HZ; H6; 1H); 2n: 1.34 (d; 3JHH = 7.1 Hz; CH3CH2O; 6H); 3.20 (s; CH3SO2; 3H); 4.13 (m; CH3CH2O; 4H); 7.40 (dd; 3JHH = 8.5 Hz; 4JHP = 3.4 Hz; H2 et H6); 7.90 (dd; 3JHH = 8.5 Hz; 3JHP = 12.8 Hz; H3 et H5); 2o: 1.38 (t; 3JHH = 7.0 Hz; (O-CH2-CH3)2; 6H); 4.2 (m; (O-CH2-CH3)2; 4H); 5.14 (ddd; 3JHH = 3JHH = 6.2 Hz; 4JHH = 2.7 HZ; 2H; H3); 5.58 (t; 3JHH = 6.2 Hz; 1H; H4); 5.79 (dd; 3JHH = 6.2 Hz; 3JHP = 9.1 Hz; 2H; H2)
  • 13C NMR spectra of new products, 2k: 16.36 (d; 3JCP = 6.3 Hz; (O-CH2-CH3)2); 62.31 (d; 2JCP = 5.4 Hz; (O-CH2-CH3)2); 64.12 (d; 3JCP = 3.6 Hz; -CH2-O-CO); 126.56 (d; 1JCP = 183.1 Hz; C1); 127.70 and 128.83 (2d; 3JCP = 14.4 Hz; C3 and C5); 132.78 (d; 4JCP = 2.7 Hz; C4); 134.19 (d; 2JCP = 9.9 Hz; C6); 139.43 (d; 2JCP = 9.9 Hz: C2); 170.62 (s; C(O)); 21: 16.39 (d; 3JCP = 6.3 Hz; (O-CH2-CH3)2); 58.68 (s; O-CH3); 62.19 (d; 2JCP = 5.4 Hz; (O-CH2-CH3)2); 72.09 (d; 3JCP = 2.7 Hz; -CH2-O); 125.50 (d; 1JCP = 183.5 Hz; C1); 127.02 and 128.10 (2d; 3JCP = 14.4 and 13.5 Hz; C3 and C5); 128.59 (d; 2JCP = 12.6 Hz; C2); 133.73 (d; 2JCP = 9.9 Hz; C6); 132.74 (d; 4JCP = 2.7 Hz; C4); 2n: 16.31 (d; 3JCP = 6.3 Hz; (O-CH2-CH3)2); 62.53 (d; 2JCP = 6.3 Hz; (O-CH2-CH3)2); 129.35 (d; 3JCP = 15.2 Hz; C3); 132.39 (d; 2JCP = 9.87 Hz; C2); 134.79 (d; 1JCP = 185.8 Hz; C1); 138.75 (d; 4JCP = 3.6 Hz; C4); 191.68 (s; C(O)H); 2o: 16.40 (d; 3JCP = 6.3 Hz; CH3-CH2-O); 37.92 (s; CH3SO2); 62.50 (d; 2JCP = 5.5 Hz; CH3-CH2-O); 122.21 (d; 3JCP = 16.2 Hz; C2 et C6); 128.00 (d; 1JCP = 190.2 Hz; C4); 134.00 (d; 2JCP = 10.8 Hz; C3 et C5); 152.11 (d. 4JCP = 3.6 Hz; C1)
  • Chauvin , R. 1990 . J. Organometal. Chem. , 387 C1(.
  • Deemie , R. W. and Knight , D. A. 1997 . Inorg. Chim. Acta , 254 : 163
  • Lu , X. and Zhu , J. 1987 . Synthesis , : 726

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