Cyanide as an Efficient and Mild Catalyst in the Aminolysis of Esters

Journal of Organic Chemistry

Volumn 52, Issue 10, 1987, Pages 2033-2036

  Högberg, Thomas ^a   Strüm, Peter ^a   Ebner, Michael ^a   Rämsby, Sten ^a  

^a Medicinal Chemistry   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845283356     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00386a025     Document Type: Article

References (32)

1. Federsel, H. J. ; Hogberg, T.; Ramsby, S.; Strom, P. Swedish Patent Application 8 602 339–337, 1986.
2. Hogberg, T.; Ulff, B. J. Org. Chem. 1984, 49, 4209–4214.
3. Beckwith, A. L. J. In The Chemistry of Amides; Zabicky, J. Ed.; Wiley-Interscience: New York, 1970; pp 96–109.
4. Stern, E. S. Chem. Ind. (London) 1956, 277.
5. Singh, B. Tetrahedron Lett. 1971, 321–322.
6. Betts, R. L.; Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 1568–1572.
7. Bodroux, F. Bull. Soc. Chim. Fr. 1905, 33, 831.
8. Yang, K. W. ; Cannon, J. G.; Rose, J. G. Tetrahedron Lett. 1970, 1791–1794.
9. Openshaw, H. T.; Whittaker, N. J. Chem. Soc. C 1969, 89–91.
10. Nakamizo, N. Bull. Chem. Soc. Jpn. 1971, 44, 2006.
11. Watanabe, Y.; Mukaiyama, T. Chem. Lett. 1981, 285–288.
12. Petit, J.; Poisson, R. C. R. Hebd. Seances Acad. Sci. 1958, 247, 1628.
13. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 18, 4171–4174.
14. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616–5617.
15. The chemistry of acyl cyanides has been thoroughly reviewed. Hunig, S.; Schaller, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 36–49.
16. Hibbert, F.; Satchell, D. P. N. J. Chem. soc., B. 1968, 565-568.
17. Ide, W. S.; Buck, J. S. Org. React. 1948, 4, 269–304.
18. Stetter, H. Angew. Chem., Int. Ed. Engl. 1976. 15. 639–647.
19. Jones, D. S.; Kenner, G. W.; Sheppard, R. C. J. Chem. Soc. 1965, 4393–4396.
20. Murahashi, S. I. ; Naota, T.; Nakajima, N. Tetrahedron Lett. 1985, 26, 925–928.
21. Hofle, G.; Steglich, W.; Vorbriiggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569–583.
22. Cf. the high reactivity of N,N-dialkylhydroxylamine esters as acylating agents in reactions that are subject to acid catalysis. Handford, B. O.; Jones, J. H.; Young, G. T.; Johnson, T. F. N. J. Chem. Soc. 1965, 6814–6827.
23. Fellinger, L. L.; Audrieth, L. F. J. Am. Chem. Soc. 1938, 60, 579–581.
24. Audrieth, L. F.; Scott, L. D.; Hill, O. F. J. Am. Chem. Soc. 1942, 64, 2498–2499.
25. Audrieth, L. F.; Kleinberg, J. J. Org. Chem. 1938, 3, 312–316.
26. Williams, J. W.; Rainey, W. T.; Leopold, R. S. J. Am. Chem. Soc. 1942. 64. 1738–1739.
27. Bottcher, B.; Bauer, F. Justus Liebigs Ann. Chem. 1950, 568, 218–227.
28. Oxley, P.; Partridge, M. W.; Robson, T. D.; Short, W. F. J. Chem. Soc. 1946. 763–771.
29. King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1946, 68, 632–636.
30. Taverne, H. J. Recl. Trav. Chim. Pays-Bas Belg. 1897,16, 33–43.
31. Woodbury, R. P.; Rathke, M. W. J. Org. Chem. 1977, 42, 1688–1690.
32. Pfeiffer, P.; Epler, H. Justus Liebigs Ann. Chem. 1940, 545, 263–286.