Unusual solvent-dependent behaviour of hydroxyiminophosphonamidates in the Beckmann reactions: Choice between rearrangement or fragmentation to metaphosphonamidate species

Chemical Communications

Volumn , Issue 18, 1997, Pages 1751-1752

  Kehler, Jan ^a,b   Breuer, Eli ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542580079     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704787h     Document Type: Article

References (21)

1. E. Breuer, H. Zaher, Z. Tashma and D. Gibson, Heteroatom Chem., 1996, 7, 151.
2. R. E. Gawley, Org. React., 1988, 35, 1; other recent references to reviews of the Beckmann reactions are cited in ref. 3.
3. M. T. Nguyen, G. Raspoet and L. G. Vanquickenborne, J. Am. Chem. Soc., 1997, 119, 2552.
4. A. C. Satterthwait and F. H. Westheimer, J. Am. Chem. Soc., 1978, 100, 3197; J. M. Friedman, S. Freeman and J. R. Knowles, J. Am. Chem. Soc., 1988, 110, 1267.
5. A. C. Satterthwait and F. H. Westheimer, J. Am. Chem. Soc., 1978, 100, 3197; J. M. Friedman, S. Freeman and J. R. Knowles, J. Am. Chem. Soc., 1988, 110, 1267.
6. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
7. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
8. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
9. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
10. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
11. F. Ramirez and J. F. Marecek, Tetrahedron, 1979, 35, 1581; 1980, 36, 3151; J. M. Friedman and J. R. Knowles, J. Am. Chem. Soc., 1985, 107, 6126; M. J. P. Harger and A. Smith, J. Chem. Soc., Perkin Trans. 1, 1990, 2507; M. P. Coogan and M. J. P. Harger, J. Chem. Soc., Chem. Commun., 1990, 1745; S. Jankowski and L. D. Quin, J. Am. Chem. Soc., 1991, 113, 7011.
12. s = -0.39 for butan-1-ol: R. W. Taft, Jr., J. Am. Chem. Soc., 1952, 74, 3120.
13. Such species have been observed previously in the fragmentation of other metaphosphate precursors in aprotic solvents: F. Ramirez, J. F. Marecek and S. S. Yemul, J. Am. Chem. Soc., 1982, 104, 1345; E. Breuer, M. Mahajna, L. D. Quin and G. S. Quin, J. Org. Chem., 1991, 56, 4791; M. Mahajna and E. Breuer, J. Org. Chem., 1993, 58, 7822.
14. Such species have been observed previously in the fragmentation of other metaphosphate precursors in aprotic solvents: F. Ramirez, J. F. Marecek and S. S. Yemul, J. Am. Chem. Soc., 1982, 104, 1345; E. Breuer, M. Mahajna, L. D. Quin and G. S. Quin, J. Org. Chem., 1991, 56, 4791; M. Mahajna and E. Breuer, J. Org. Chem., 1993, 58, 7822.
15. Such species have been observed previously in the fragmentation of other metaphosphate precursors in aprotic solvents: F. Ramirez, J. F. Marecek and S. S. Yemul, J. Am. Chem. Soc., 1982, 104, 1345; E. Breuer, M. Mahajna, L. D. Quin and G. S. Quin, J. Org. Chem., 1991, 56, 4791; M. Mahajna and E. Breuer, J. Org. Chem., 1993, 58, 7822.
16. J. B. Lambert, R. W. Emblidge and Y. Zhao, J. Org. Chem., 1994, 59, 5397; J. B. Lambert and Y. Zhao, J. Am. Chem. Soc., 1996, 118, 3156; E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev and H. Leader, J. Chem. Soc., Perkin Trans. 1. 1990, 3263; E. Breuer, H. Zaher and Z. Tashma, Tetrahedron Lett., 1992, 33, 2067; E. Breuer and C. J. Solomon, J. Org. Chem., 1997, 62, 3858.
17. J. B. Lambert, R. W. Emblidge and Y. Zhao, J. Org. Chem., 1994, 59, 5397; J. B. Lambert and Y. Zhao, J. Am. Chem. Soc., 1996, 118, 3156; E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev and H. Leader, J. Chem. Soc., Perkin Trans. 1. 1990, 3263; E. Breuer, H. Zaher and Z. Tashma, Tetrahedron Lett., 1992, 33, 2067; E. Breuer and C. J. Solomon, J. Org. Chem., 1997, 62, 3858.
18. J. B. Lambert, R. W. Emblidge and Y. Zhao, J. Org. Chem., 1994, 59, 5397; J. B. Lambert and Y. Zhao, J. Am. Chem. Soc., 1996, 118, 3156; E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev and H. Leader, J. Chem. Soc., Perkin Trans. 1. 1990, 3263; E. Breuer, H. Zaher and Z. Tashma, Tetrahedron Lett., 1992, 33, 2067; E. Breuer and C. J. Solomon, J. Org. Chem., 1997, 62, 3858.
19. J. B. Lambert, R. W. Emblidge and Y. Zhao, J. Org. Chem., 1994, 59, 5397; J. B. Lambert and Y. Zhao, J. Am. Chem. Soc., 1996, 118, 3156; E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev and H. Leader, J. Chem. Soc., Perkin Trans. 1. 1990, 3263; E. Breuer, H. Zaher and Z. Tashma, Tetrahedron Lett., 1992, 33, 2067; E. Breuer and C. J. Solomon, J. Org. Chem., 1997, 62, 3858.
20. J. B. Lambert, R. W. Emblidge and Y. Zhao, J. Org. Chem., 1994, 59, 5397; J. B. Lambert and Y. Zhao, J. Am. Chem. Soc., 1996, 118, 3156; E. Breuer, A. Schlossman, M. Safadi, D. Gibson, M. Chorev and H. Leader, J. Chem. Soc., Perkin Trans. 1. 1990, 3263; E. Breuer, H. Zaher and Z. Tashma, Tetrahedron Lett., 1992, 33, 2067; E. Breuer and C. J. Solomon, J. Org. Chem., 1997, 62, 3858.
21. For a recent review on oxyiminophosphonates, see E. Breuer, in The chemistry of organophosphorus compounds, ed. F. R. Hartley, Wiley, New York, 1996, vol. 4, pp. 653-729.