Reactions of Palladium(II) Chloride with Aziridine Rings. Catalytic Rearrangement of N-Carbethoxy-8-azabicyclo[5.1.0]oct-3-ene to N-Carbethoxynortropidine

Journal of the American Chemical Society

Volumn 98, Issue 14, 1976, Pages 4168-4174

  Wiger, George R ^a   Rettig, Michael F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001249338     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00430a027     Document Type: Article

References (29)

1. G. Albelo and M. F. Rettig, J. Organomet. Chem., 42, 183 (1972).
2. G. Albelo, G. Wiger, and M. F. Rettig, J. Am. Chem. Soc., 97, 4510 (1975).
3. J. March, “Advanced Organic Chemistry: Reactions, Mechanisms and Structure”, McGraw-Hill, New York, N. Y. 1968.
4. O. C. Dermer and G. E. Ham, “Ethyleneimine and Other Aziridines: Chemistry and Applications”, Academic Press, New York, N. Y., 1969.
5. L. A. Paquette, “Principles of Modern Heterocyclic Chemistry”, W. A. Benjamin, New York, N. Y., 1968.
6. H. C. Van Der Plas, “Ring Transformations of Heterocycles”, Vol. 1, Academic Press, New York, N. Y., 1973.
7. R. Grigg and G. Shelton, Chem. Commun., 1247 (1971).
8. G. Adames, C. Blbby, and R. Grigg, J. Chem. Soc., Chem. Commun., 491 (1972).
9. R. Grigg, R. Hayes, and A. Sweeney, Chem. Commun., 1248 (1971).
10. T. Fujisawa, K. Sujimoto, and H. Ohta, Chem. Lett., 883 (1974).
11. K. B. Sharpless, M. A. Umbreit, M. T. Nieh, and T. C. Flood, J. Am. Chem. Soc., 94, 6538 (1972).
12. R. Aumann and H. Averbeck, J. Organomet. Chem., 45, C4 (1975).
13. R. Aumann, K. Frohlich, and H. Ring, Angew. Chem. Int. Ed. Engl., 13, 275 (1974).
14. G. Fodor in “The Alkaloids”, Vol. XIII, R. H. F. Manske, Ed., Academic Press, New York, N. Y., 1971, Chapter 8.
15. J. E. Saxton in “A Specialist Periodical Report: The Alkaloids”, Vol. 4, J. E. Saxton, Sr. Reporter, the Chemical Society, London, 1974, Chapter 3.
16. M. Kubota, B. A. Denechaud, P. M. McKinney, T. E. Needham, and G. O. Spessard, J. Catal., 119 (1970).
17. J. E. Dewhurst, J. J. Kaminski, and J. H. Supple, J. Heterocycl. Chem., 9, 507 (1972).
18. S. J. Daum, C. M. Martini, R. K. Kullnig, and R. L. Clarke, J. Org. Chem., 37, 1665 (1972).
19. A. Sinnema, L. Maat, A. J. Van Der Gugten, and H. C. Beyerman, Reel. Trav. Chlm. Pays-Bas, 87, 1027 (1968).
20. R. M. Silverstein and G. C. Bassler, “Spectrophotometric Identification of Organic Compounds”, 2d ed, Wiley, New York, N. Y., 1967.
21. E. Vedejs and M. F. Salomon, J. Am. Chem. Soc., 92, 6965 (1970).
22. G. Wiger, G. Albelo and M. F. Rettig, J. Chem. Soc., Dalton Trans., 2242 (1974).
23. P. M. Maitlis, “The Organic Chemistry of Palladium”, Vol. 1 and 2, Academic Press, New York, N. Y., 1971.
24. J. K. Stille and D. E. James, J. Am. Chem. Soc., 97, 675 (1975).
25. J. D. Hobson and W. D. Riddell, Cham. Commun., 1178 (1968).
26. L. F. Hines and J. K. Stills, J. Am. Cham. Soc., 94, 485 (1972).
27. J. X. McDermott and G. M. Whitesides, J. Am. Chem. Soc., 96, 947 (1974).
28. J. X. McDermott, J. F. White, and G. M. Whitesides, J. Am. Chem. Soc., 95, 4451 (1973).
29. H. Dirkzwager, T. J. Nieuwstad, A. M. VanWijk, and H. Van Bekkum, Rad. Trav. Chim. Pays-Bas, 92, 35 (1973).