Conversion of primary amides to nitriles by aldehyde-catalyzed water transfer

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6486-6487

  Heck, Marie Pierre ^a   Wagner, Alain ^b   Mioskowski, Charles ^a,b  

^a DIF   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000473455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961128v     Document Type: Article

References (43)

1. (a) Kent, R. E.; McElvain, S. M. Org. Synth. 1945, 25, 61.
2. (b) Mowry, D. T. Chem. Rev. 1948, 42, 189.
3. (a) Patai, S. In The Chemistry of Functional Groups: Amides; Zabicky, J., Ed.; John Wiley and Sons: New York, 1970.
4. (b) Larock, R. C. Comprehensive Organic Transformations; VCH Publishers, Inc.: New York, 1989.
5. (a) Humber, L. G.; Davis, M. A. Can. J. Chem. 1966, 44, 2113.
6. (b) Reisner, D. B.; Horning, E. C. Organic Syntheses; Wiley: New York, 1963; Collect. Vol IV, p 144.
7. (a) Reid, W. B., Jr.; Hunter, J. H. J. Am. Chem. Soc. 1948, 70, 3515.
8. (b) Friedrich, K.; Gallmeier, H. J. Tetrahedron Lett. 1981, 22, 2971.
9. (c) Yamada, S.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1976, 1, 57.
10. (d) Yates, P.; Bichan, D. J. Can. J. Chem. 1975 53, 2045.
11. (a) McElvain, S. M.; Stevens, C. L. J. Am. Chem. Soc. 1947, 69, 2663.
12. (b) Neuman, M. S.; Arkell, A.; Fuknaga, T. J. Am. Chem. Soc. 1960, 82, 2498.
13. (c) Cram, D. J.; Haberfield, P. J. Am. Chem. Soc. 1961, 83, 2363.
14. (d) Rickborn, B.; Jensen, F. R. J. Org. Chem. 1962, 27, 4608.
15. (e) Krynitsky, J. A.; Carhart, H. W. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. IV, p 436.
16. (f) Baldwin, J. E.; Carter, C. G. J. Org. Chem. 1983, 48, 3912.
17. (g) Ressler, C.; Nagarajan, G. R.; Kirisawa, M.; Kashelikar, D. V. J. Org. Chem. 1971, 36, 3960.
18. (h) Ressler, C.; Kashelikar, D. V. J. Am. Chem. Soc. 1966, 88, 2025.
19. (a) Sznaidman, M. L.; Crasto, C.; Hecht, S. M. Tetrahedron Lett. 1993, 34, 1581.
20. (b) Rigo, B.; Lespagnol, C.; Pauly, M. J. Heterocycl. Chem. 1986, 23, 183.
21. (c) Rigo, B.; Lespagnol, C.; Pauly, M. Tetrahedron Lett. 1986, 27, 347.
22. (d) Campagna, F.; Carroti, A.; Casini, G. Tetrahedron Lett. 1977, 21, 1813.
23. (a) Stephens, C. R.; Bianco, E. J.; Picgrin, F. J. J. Am. Chem. Soc. 1955, 77, 1701.
24. (b) Pesson, M. Bull. Soc. Chim. Fr. 1965, 2262.
25. (c) Yamamoto, E.; Sugasawa, S. Tetrahedron Lett. 1970, 4383.
26. (d) Snatzke, G.; Klein, H. Chem. Ber. 1972, 105, 244.
27. (e) Ficken, G. E.; France, H.; Linstead, R. P. J. Chem. Soc. 1954, 3731.
28. (a) Bagar, T. M.; Riley, C. M. Synth. Commun. 1980, 10, 479.
29. (b) Saednya, A. Synthesis 1985, 184.
30. (c) Mai, K., Patil, G. Tetrahedron Lett. 1986, 27, 2203.
31. (d) Lehnert, W. Tetrahedron Lett. 1971, 1501.
32. (a) Saraie, T.; Ishiguro, T.; Kawashima, K.; Morita, K. Tetrahedron Lett. 1973, 2121.
33. (b) Denis, W. E. J. Org. Chem. 1970, 35, 3253.
34. (c) Olah, G. A.; Narang, S. C.; Fung, A. P.; Gupta, B. C. G. Synthesis 1980, 657.
35. (d) Ressler, C.; Ratzkin, H. J. Org. Chem. 1961, 26, 3356.
36. (a) Correia, J. Synthesis 1994, 1127.
37. (b) Correia, J. J. Org. Chem. 1992, 57, 4555.
38. (a) Kim, S.; Yi, K. Y. Tetrahedron Lett. 1986, 22, 1925.
39. (b) Yokoyama, M.; Yoshida, S.; Imamoto, T. Synthesis 1982, 591.
40. (c) Hendrickson, J. B.: Schwartzman, S. M. Tetrahedron Lett. 1975, 277.
41. (d) Cooper, D.; Trippett, S. Tetrahedron Lett. 1979, 19, 1725.
42. Heck, M. P.; Monthiller S.; Mioskowski, C. Unpublished results.
43. 4, filtered, and concentrated. The 3-phenylpropanonitrile crude was purified as described above (Procedure A). The spectral data were identical with those of commercially available product.