Reactions of N-acylaziridines with sodium metal and sodium naphthalenide. Elimination of olefines

Journal fur Praktische Chemie - Chemiker - Zeitung

Volumn 338, Issue 3, 1996, Pages 270-278

  Lin, Pen Yuan ^a   Bellos, Konstantinos ^b   Werry, Jürgen ^b   Assithianakis, Petros ^b   Weiß, Rainer ^b   Mall, Thomas ^b   Bentz, Gunther ^b   Stamm, Helmut ^b  

^a TAIPEI MEDICAL UNIVERSITY   (Taiwan)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346176608     PISSN: 09411216     EISSN: None     Source Type: Journal    
DOI: 10.1002/prac.19963380153     Document Type: Article

References (32)

1. (a) Part 68: J. Werry, P.-Y. Lin, P. Assithianakis, H. Stamm, J. Chem. Soc., Perkin Trans. 1, in the press;
2. (b) Part 67: K. Bellos, H. Stamm, J. Org. Chem. 60 (1995) 5661; (c) Part 66 = [14]
3. H. Stamm, P. Assithianakis, R. Weiß, G. Bentz, B. Buchholz, J. Chem. Soc., Chem. Comm. 1984, 753
4. P.-Y. Lin, J. Werry, G. Bentz, H. Stamm, J. Chem. Soc., Perkin Trans. 1 1993, 1139
5. D. Archier-Jay, N. Besbes, A. Laurent, E. Laurent, S. Lesniak, R. Tardivel, Bull. Soc. Chim. Fr. 1989, 537
6. (a) H. Stamm, T. Mall, R. Falkenstein, J. Werry, D. Speth, J. Org. Chem. 54 (1989) 1603;
7. (b) H. Stamm, A. Sommer, A. Woderer, W. Wiesert, T. Mall, P. Assithianakis, J. Org. Chem. 50 (1985) 4946
8. J. F. Garst, C. D. Smith, J. Am. Chem. Soc. 98 (1976) 1520
9. J. F. Garst, Accounts Chem. Res. 4 (1971) 400
10. A. Hassner, A. Kascheres, Tetrahedron Lett. 1970, 4623
11. -1 has been found for hydrogen abstraction from THF by cyclopropyl radical: L. J. Johnston, J. C. Scaiano, K. U. Ingold, J. Am. Chem. Soc. 106 (1984) 4877.
12. -1 for a tertiary radical: M. Newcomb, S. U. Park, J. Am. Chem. Soc. 108 (1986) 4132
13. -1: M. Newcomb, A. G. Glenn, J. Am. Chem. Soc. 111 (1989) 275
14. M. Vora, M. Holy, J. Org. Chem. 40 (1975) 3144
15. 3 when alcohol concentration is low: E. C. Steiner, J. M. Gilbert, J. Am. Chem. Soc. 85 (1963) 3054;
16. D. Alprim, J. E. Bares, J. C. Branco, F. G. Bordwell, J. Org. Chem. 43 (1978) 5024.
17. Intramolecular protonation of an alkoxide by a (particular) benzyl group has been described: S. Bradamante, R. Ferraccioli, G. A. Pagani, J. Chem. Soc., Perkin Trans. 1 1987, 515.
18. N. Hirahota, Metal Ketyls and Related Radical Ions - Electronic Structures and Ion Pair Equilibria, in: Radical Ions, Ed.: E. T. Kayser, L. Kevan, Part of the series: Reactive Intermediates in Organic Chemistry, Ed.: G. A. Olah, J. Friedman, Interscience Publishers, New York 1968, p. 52-58
19. K. Bellos, H. Stamm, J. Prakt. Chem. 335 (1995) 269
20. Elimination of NaH from anions of dihydronaphthalens has been described: S. Bank, T. A. Lois, M. C. Prislopski, J. Am. Chem. Soc. 91 (1969) 5407
21. and lit. cited therein. Analogous formulation of LiH elimination: R. L. Eppley, J. A. Dixon, J. Am. Chem. Soc. 90 (1968) 1606
22. J. Werry, H. Stamm, P.-Y. Lin, R. Falkenstein, G. Fries, H. Irngartinger, Tetrahedron 45 (1989) 5015
23. H. Stamm, D. Speth, Chem. Ber. 122 (1989) 1795
24. E. K. Raunio, W. A. Bonner, J. Org. Chem. 31 (1966) 396
25. H. Stamm, R. Falkenstein, Chem. Ber. 123 (1990) 2227
26. Cp.: V. Rautenstrauch, Tetrahedron 44 (1988) 1613
27. P. Mackiewicz, R. Furstoss, Tetrahedron 34 (1978) 3241, 3253;
28. R. S. Neale, Synthesis 1971, 1
29. H. E. Baumgarten, F. A. Bower, R. A. Setterquist, R. E. Allen, J. Am. Chem. Soc. 80 (1958) 4588
30. J. F. Bieron, F. J. Dinan, in: Chemistry of Amides, Ed.: J. Zabicky, Interscience Publishers, London, New York, 1970, p. 280
31. B. Buchholz, H. Stamm, Isr. J. Chem. 27 (1986) 17
32. D. V.-Kashelikar, P. E. Fanta, J. Org. Chem. 26 (1961) 1841