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Tytuł artykułu
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Języki publikacji
Abstrakty
Oxidation of 1- and 2-substituted naphthalenes (1) with 30% hydrogen peroxide in the presence of poly(bis-1,2-diphenylene) diselenide (PPDS) has been investigated. Depending on the substrate used trans-2-carboxycinnamic acid (2), and its isomer, (1-oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid (3) or 2-naphthoic acid (4b) was a major product. Oxidation of hydroxynaphthalenes 1b and 1c is a convenient way to obtain trans-2-carboxy cinnamic acid (2) in almost quantitative yield. The mechanism of the reaction is postulated.
Słowa kluczowe
Wydawca
Czasopismo
Rocznik
Tom
Strony
231--248
Opis fizyczny
Bibliogr. 25 poz., rys.
Twórcy
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wyb. Wyspianskiego 27, 50-370 Wrocław, Poland
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wyb. Wyspianskiego 27, 50-370 Wrocław, Poland
autor
- Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wyb. Wyspianskiego 27, 50-370 Wrocław, Poland
Bibliografia
- 1. Franz G. and Sheldon R.A., Ullman's Encyclopedia of Industrial Chemistry, WILEY-VCH, Weinheim, 2003 vol. 24, p. 487.
- 2. Weissermal K. and Arpe H.-J., Industrial Organic Chemistry, VCH, Weinheim 1993, p. 236,344,381.
- 3. Jones A.K. and Wilson T.E., in Encyclopedia ofReagents for Organic Synthesis, Paquette L.A. (ed.), J. Wiley & Sons 1995, p. 880.
- 4. Młochowski J. and Said S.B., Polish J. Chem., 71,140 (1997).
- 5. Młochowski J., Brz^szcz M., Giurg M., Palus J. and Wojtowicz H., Eur. J. Org. Chem., (2003) in press.
- 6. Wójtowicz H., Brzaszcz M., Kloc K. and Mlochowski J., Tetrahedron, 57, 9743 (2001).
- 7. Giurg M., Said S.B., Syper L. and Mlochowski J., Synth. Commun., 31, 3151 (2001).
- 8. Giurg M., Mlochowski J. and Ambroiak A., Polish J. Chem., 76,1713 (2002).
- 9. Młochowski J., Giurg M., Kubicz E. and Said S.B., Synth. Commun., 26, 291 (1996).
- 10. Młochowski J. and Giurg M., Polish J. Chem., 68, 2333 (1994).
- 11. Sonoda N. and Tsutsumi S., Technol Rept. Osaka Univ., 14,977 (1965); Chem. Abstr., 62,16178-16179 (1965).
- 12. Sawaki Y. and Foote C.S., J. Am. Chem. Soc., 105, 5035 (1983).
- 13. Adam W. and Ganeshpure P.A., Synthesis, 280 (1993).
- 14. Haarmaan D.G. and Holzminder R.G., Ullman s Encyklopedia of Industrial Chemistry WILEY-VCH, Weinheim, 2003, vol. 8, p. 521.
- 15. Raacke-Fels I.D., Wang C.H., Robins R.K. and Christensen B.E., J. Org. Chem., 15,627 (1950).
- 16. Ames G.R. and Davey W., J. Org. Chem., 23,1794 (1958).
- 17. Młochowski J., Chem. Papers, 58,45 (1998).
- 18. Ten Brink G.-J., Vis J.-M., Arends I.W.C.E. and Sheldon R.A., Tetrahedron, 58, 3977 (2002).
- 19. Brzaszcz M., Kloc K., Maposah M. and Mlochowski J., Synth. Commun., 30, 4425 (2000).
- 20. Ehrlich E. and Benedikt R., Monatsh. Chem., 9, 527 (1888).
- 21. Shirley D.A. and Cheng C.F., J. Organomet. Chem., 20, 251 (1969).
- 22. Kiefel C. and Mannschreck A., Synthesis, 1033 (1995).
- 23. Schlosser M., Eur. J. Org. Chem., 3975 (2001).
- 24. Betz J. and Bauer W., J. Am. Chem. Soc., 124, 8699 (2002).
- 25. Narasimhan N.S. and Mali L.S., Tetrahedron, 31, 1005 (1975).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0023-0165