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Abstrakty
Treatment of chromone-2, coumarin-4 and pyrone-2 derivatives of N-benzylaminomethylphosphonic acid with strong mineral acids leads to formation of the corresponding heterocyclic amines and phosphoric acid. Kinetic studies of this cleavage reaction demonstrate that protonation has a remarkable influence on a cleavage of C-P bonds. In aq. H2SO4, cleavage of the acids 1-3 exhibits a kinetic dependence on [H+]. The measured solvent isotope effect (kH/kD) was about 1.5 for the 1 and 2 and only 1.1 for the 3. The existence of the isotope effect shows that protons are involved on the rate-determining step. The data obtained suggest that the protonated phosphonate molecule is split by a dissociative mechanism with A-SE2 character and this is combined with an elimination of the phosphonate group as a positive-charged phosphorus moiety.
Wydawca
Czasopismo
Rocznik
Tom
Strony
63--69
Opis fizyczny
Bibliogr. 13 poz., rys.
Twórcy
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, 50-370 Wroclaw, Poland
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, 50-370 Wroclaw, Poland
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wroclaw University of Technology, 50-370 Wroclaw, Poland
Bibliografia
- 1. Boduszek B„ Lipiński M. and Kowalska M., Phosphorus, Sulfur and Silicon, 143, 179(1998).
- 2. Boduszek B. and Uher M., Synth. Commun., 30, 1749 (2000).
- 3. Boduszek B., Tetrahedron, 52, 12483 (1996).
- 4. Boduszek B., Latajka R. and Leśniak W., Phosphorus, Sulfur and Silicon, (inpress).
- 5. Long F.A. and Paul M.A., Chem. Rev., 57, 935 (1957).
- 6. Westheimer F.H., Chem. Rev., 81, 313 (1981).
- 7. Quin L.D., Coordination Chem. Rev., 137, 525 (1994).
- 8. Michaelis A., Ann., 293, 193 (1896).
- 9. Nagarajan K., Sheliy K.P., Perkins R.R. and Stewart R., Can. J. Chem., 65, 1729 (1987).
- 10. Skrzypczyński Z., J. Phys. Org. Chem., 3, 23 (1990), ibid. 3, 35 (1990).
- 11. Schaleger L.L. and Long F.A., Adv. Phys. Org. Chem., 1, 1 (1963).
- 12. Johnson C.D., Katritzky A.R. and Shapiro S.A., J. Am. Chem. Soc., 91, 6654 (1969).
- 13. Kreevoy M.M., J. Am. Chem. Soc., 79, 5927 (1957).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0016-0060