The 'in situ' generation of fluorinated aldehydes and consecutive reactions with P- and N-nucleophiles

Journal of Fluorine Chemistry

Volumn 81, Issue 1, 1996, Pages 75-82

  Haas, Andreas M ^a   Hägele, Gerhard ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

DIBAL; Fluorinated aldehydes; Fluorinated hydroxyethane phosphonic acid esters; Fluorinated N (phenylamino) ethane phosphonic acid esters; NMR spectroscopy

Indexed keywords

EID: 9144258002     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-1139(96)03432-x     Document Type: Article

References (27)

1. [1] G. Hägele and A.M. Haas, J. Fluorine Chem., 76(1995) 15-19.
2. [2] G. Resnati, Tetrahedron, 49 (1993) 9385.
3. [3] (a) J.T. Welch, Tetrahedron, 43 (1987) 3123;
4. (b) J. Mann, Chem. Soc. Rev., 16 (1987) 381;
5. (c) A. Haas and M.R.C. Gerstenberger, Angew. Chem., 93 (1981) 659.
6. [4] (a) J. Oleksyszyn and L. Subotkowska, Synthesis, (1980) 906;
7. (b) J. Oleksyszyn, R. Tyka and P. Mastalerz, Synthesis, (1978) 479.
8. [5] (a) U. Gruß and G. Hägele, Phosphorus, Sulphur, Silicon, 97 (1994) 209;
9. (b) K. Issleib, K.P. Döpfer and A. Balszuweit, Phosphorus, Sulfur, 14 (1983) 171.
10. [6] (a) J. Oleksyszyn, E. Gruszecka, P. Kafarski and P. Mastalerz, Monatsh. Chem., 113 (1982) 59;
11. (b) K.D. Berlin, R.T. Claunch and E.T. Gaudy, J. Org. Chem., 33 (1968) 3090.
12. [7] (a) V.S. Abramov, Zh. Obshch. Khim., 22 (1952) 647;
13. (b) T. Gajda, Synthesis, (1990) 717;
14. (c) T. Gajda, Phosphorus, Sulfur, Silicon, 53 (1990) 327.
15. [8] (a) T. Ishihara, T. Maekawa and T. Ando, Tetrahedron Lett., 25 (1984) 1377;
16. (b) T. Ishhara, T. Maekawa and T. Ando, Tetrahedron Lett., 24 (1983) 4229.
17. [9] (a) T. Ishihara, T. Maekawa, Y. Yamasaki and T. Ando, J. Fluorine Chem., 34 (1986) 271;
18. (b) T. Ishihara, T. Maekawa, Y. Yamasaki and T. Ando, J. Fluorine Chem., 34 (1986) 323;
19. (c) P. Mastalerz, in R. Engel (ed.), Handbook of Organophosphorus Chemistry, Marcel Dekker Inc., New York. 1992, Chap. 7, p. 3.3.
20. [10] K. Tamura, H. Mizukami, K. Maeda, H. Watanabe and K. Uneyama, J. Org. Chem., 58 (1993) 32.
21. [11] G.A. Flynn, D.W. Beight, E.H.W. Bohme and B.W. Metcalf, Tetrahedron Lett., 26 (1985) 285.
22. [12] A. Ayi and R. Guedj, J. Chem. Soc., Perkin Trans. 1, (1983) 2045.
23. [13] J. Zygmunt, Tetrahedron, 41 (1985) 4979.
24. [14] S. Kiyooka and M. Shirouchi, J. Org. Chem., 57 (1992) 1.
25. [15] P.G. Baraldi, M. Guarneri, F. Moroder, G.P. Pollini and D. Simoni, Synthesis, (1986) 653.
26. [16] H. Suga and M. Schlosser, Tetrahedron, 46 (1990) 4261.
27. [17] S. Kaneko, T. Yamazaki and T. Kitazume, J. Org. Chem., 58 (1993) 2302.