Meerwein's catalytic Beckmann rearrangement

Journal fur Praktische Chemie - Chemiker - Zeitung

Volumn 338, Issue 5, 1996, Pages 460-467

  Shrestha Dawadi, P B ^a   Hitzler, M G ^a   Lutz, M ^a   Jochims, J C ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042940136     PISSN: 09411216     EISSN: None     Source Type: Journal    
DOI: 10.1002/prac.19963380188     Document Type: Article

References (33)

1. E. Beckmann, Ber.Dtsch.Chem.Ges. 19 (1886) 988
2. R. E. Gawley, Org.React. 35 (1988) 1
3. L. G. Donaruma, W.Z. Heldt, Org.React. 11 (1960) 1
4. Ullmann's Encyclopedia of Industrial Chemistry, 5. ed., Vol.A5,31-50, VCH, Weinheim 1986
5. Kirk-Othmer, Encylopedia of Chemical Technology, 3. ed., Vol.18, 425-436, J. Wiley & Sons, New York 1982
6. Y. Izumi, Chem.Lett. 1990, 2171
7. T. Mukaiyama, T. Harada, Chem.Lett. 1991, 1652
8. T. Harada, T. Ohno, S. Kobayashi, T. Mukaiyama, Synthesis 1991, 1216
9. H. Kusama, Y. Yamashita, K. Narasaka, Bull. Chem. Soc. Jpn. 68 (1995) 373
10. H. Meerwein, Angew. Chem. 67 (1955) 374
11. M. O. Glocker, P. B. Shrestha-Dawadi, J. Küchler-Krischun, J. Hofmann, H. Fischer, J. C. Jochims, Chem.Ber. 126 (1993) 1859
12. A. F. Hegarty, Acc. Chem. Res. 13 ( 1980) 448
13. A. F. Hegarty, M. T. McCormack, G. Ferguson, P. J. Roberts, J. Am. Chem. Soc. 99 (1977) 2015
14. J. E. Johnson, S. C. Cornell, J. Org.Chem. 45 (1980) 4144
15. Details of the crystal structure determination may be obtained from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, Federal Republic of Germany, on quoting the dispository number CSD-59295, the names of the authors, and the journal citation.
16. W. Z. Heldt, J. Org. Chem. 26 (1961) 1695
17. M. I. Vinnik, N. G. Zarakhani, Russ. Chem. Rev. 36 (1967) 51
18. M. T. Nguyen, L. G. Vanquickenborne, J. Chem. Soc., Perkin Trans. 2 1993, 1969
19. P. A. Hunt, H. S. Rzepa, J. Chem. Soc., Chem.Commun. 1989, 623
20. The calculations do not support a proposal of Meisenheimer who explained the preferred migration of the C substituent trans to the leaving group by a two-step reaction: in the first step, slow rearrangement of the migrating substituent from C to N affords an N-substituted carbene, which, in a second step, undergoes fast insertion into the N-O bond: J. Meisenheimer, Ber. Dtsch. Chem. Ges. 54 (1921) 3206
21. M. G. Hitzler, M. Lutz, P. B. Shrestha-Dawadi, J. C. Jochims, Liebigs Ann. 1996, 247
22. W. E. Stewart, T. H. Siddall, Chem. Rev. 70 (1970) 517
23. D. M. Schnur, Y. H. Yuh, D. R. Dalton, J. Org. Chem. 54 (1989) 3779
24. T. Drakenberg, S. Forsén, J. Chem. Soc. Chem. Commun. 1971, 1404
25. E. Müller, D. Fries, H. Metzger. Chem. Ber. 88 (1955) 1901
26. B. Carboni, R . Carrié, Tetrahedron 40 (1984) 4115
27. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, R. de Gelder, R. Israel, J. M. M. Smits, Crystallography Laboratory, University of Nijmegen, The Netherlands, 1994.
28. H. Metzger, Methoden der Org. Chem. (Houben-Weyl) 4th ed., vol. X/4, p. 8, Thieme Verlag, Stuttgart 1968
29. L. Ruzicka, M. Kobelt, O. Häflinger, V. Prelog, Helv. Chim. Acta 32 (1949) 544
30. A. Lachman, Org. Synth., Coll. Vol. II, p. 70-72, Wiley, New York 1966
31. S. Petersen, E. Tietze, Liebigs Ann.Chem. 623 (1959) 166
32. T. Sato, H. Wakatsuka, Bull. Chem. Soc. Jpn. 42 (1969) 1955
33. J. Körösi, J. Prakt. Chem. 23 (1964) 212