Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles

Journal of Organic Chemistry

Volumn 60, Issue 9, 1995, Pages 2670-2676

  Mukhopadhyay, Manoj ^a   Reddy, M Madhava ^a   Maikap, G C ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000310993     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00114a013     Document Type: Article

References (26)

1. Iqbal, J.; Ahmad, S. Tetrahedron Lett. 1986, 27, 3791.
2. Ahmad, S.; Iqbal, J. J. Chem. Soc, Chem. Commun. 1987, 114.
3. Iqbal, J.; Srivastava, R. R. J. Org. Chem. 1992, 57, 2001.
4. Nayyar, N. K.; Reddy, M. M.; Iqbal, J. Tetrahedron Lett. 1991, 32, 6965.
5. For some recent syntheses of allyl amides and amines see: Sharpless, K. B.; Hori, T.; Truesdale, L. K.; Dietrich, C. L.J.Am. Chem. Soc. 1976, 98, 269.
6. Singer, S. P.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1448.
7. Kresze, G.; Munsterer, H. J. Org. Chem. 1983, 48, 3561; 5401.
8. Daleris, G.; Dunogues, J.; Gadras, A. Tetrahedron 1988, 44, 4243.
9. Helquist, P.; Connell, R. D.; Akermark, B. J. Org. Chem. 1989, 54, 3359.
10. Buchwald, S. L.; Watson, B. T.; Wannama-ker, M. W.; Dewan, J. C. J. Am. Chem. Soc. 1989, 111, 4486.
11. Leblanc, Y.; Zamboni, R.; Bernstein, M. A. J. Org. Chem. 1991, 56, 1971.
12. For palladium-catalyzed rearrangements of allylic acetates see: Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321.
13. Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 2301.
14. Grieco, P. A.; Tetsuo, T.; Shannon, L. B.; Hideo, T. J. Am. Chem. Soc. 1980, 102, 7587.
15. Kabore, I. Z.; Khuong-Huu, Q.; Pancrazi, A. Tetrahedron 1978, 34, 2815.
16. We have proposed a cobalt π-allyl complex from allyl acetate and cobalt(II) chloride: Bhatia, B.; Reddy, M. M.; Iqbal, J. Tetrahedron Lett. 1993, 34, 6301.
17. Maikap, G. C.; Reddy, M. M.; Mukhopadhyay, M.; Bhatia, B.; Iqbal, J. Tetrahedron 1994, 50, 9145.
18. For a similar study involving palladium complex see: Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1977, 99, 1649.
19. For thermal or metal-catalyzed rearrangements of allylic imi-dates see: Overman, L. E. Acc. Chem. Res. 1980, 13, 218.
20. For Pinner reaction see: Compagnon, P. L.; Miocque, M. Ann. Chim (Paris). 1970, 5, 23-27.
21. Ritter, J. J.; Minieri, P. P. J.Am. Chem. Soc. 1948, 70, 4045.
22. Barton, D. H. R.; Magnus, P. D.; Garbarino, J. A.; Young, R. N. J. Chem. Soc, Perkin Trans. 1 1974, 2101.
23. Krimen, L. I., Cota, D. J. Org. React. 1969, 17, 213.
24. Top, S.; Jaouen, G. J. Org. Chem. 1981, 46, 78.
25. Martinez, A. G.; Alvarez, R. M.; Villar, E. T.; Fraile, A. G.; Hanak, M.; Subramanian, L. R. Tetrahedron Lett. 1989, 30, 581.
26. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; Vogel, A. I.; ELBS: England, 1984.