N-Alkylation of Nitriles Using Chromium Tricarbonyl Complexes of Benzyl Alcohol and Its Derivatives: New Perspectives for the Ritter Reaction

Journal of Organic Chemistry

Volumn 46, Issue 1, 1981, Pages 78-82

  Top, Siden ^a   Jaouen, Gérard ^a  

^a Universite de Rennes   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001916292     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00314a017     Document Type: Article

References (35)

1. L. I. Krimen and D. J. Cota, Org. React., 17, 213 (1969).
2. F. R. Benson and J. J. Ritter, J. Am. Chem. Soc., 71, 4128 (1949);
3. E. T. Roe and D. Swen, J. Am. Chem. Soc., 75, 5479 (1953).
4. S. Top and G. Jaouen, J. Chem. Soc., Chem. Commun., 224 (1979).
5. M. Cais, Organomet. Chem. Rev., 1, 435 (1966);
6. L. Haynes and R. Pettit in “Carbonium Ions”, Vol. 5, G. A. Olah and P. V. R. Schleyer, Eds., Wiley, New York, 1975;
7. W. E. Watts, J. Organomet. Chem. Libr., 7 (1979).
8. R. F. Lockwood and K. M. Nicholas, Tetrahedron Lett., 4163 1977.;
9. S. Top, B. Caro, and G. Jaouen, Tetrahedron Lett., 787 (1978);
10. D. Seyferth, J. S. Merola, and C. E. Eschbach, J. Am. Chem. Soc., 100, 4124 1978.
11. J. D. Holmes, D. A. K. Jones, and R. Pettit, J. Organomet. Chem., 4, 324 (1965).
12. W. S. Trahanovsky and D. K. Wells, J. Am. Chem. Soc., 91, 5870 (1969).
13. N. C. Deno, P. T. Groves, J. J. Jaruzelski, and N. N. Lugasch, J. Am. Chem. Soc., 82, 4719 (1960).
14. N. C. Deno, J. J. Jaruzelski, and A. Schriesheim, J. Am. Chem. Soc., 77, 3044 (1955).
15. C. L. Parris and R. M. Christenson, J. Org. Chem., 25, 331 (1960).
16. H. Christol, A. Laurent, and G. Solladie, Bull. Soc. Chim. Fr., 877 (1963).
17. G. Glikmans, B. Torch, M. Hellin, and F. Coussemant, Bull. Soc. Chim. Fr., 1383 (1966).
18. J. J. Ritter and P. P. Minieri, J. Am. Chem. Soc., 70, 4045 (1948).
19. G. Jaouen and A. Meyer, J. Am. Chem. Soc., 97, 4667 (1975).
20. R. Huisgen and C. Rüchardt, Justus Liebigs Ann. Chem., 601, 21 (1956).
21. F. Nerdel, H. Goetz, M. Fenske, Justus Liebigs Ann. Chem., 665, 21 (1963);
22. A. Hanns, R. Clemens, German Offen. 2153 528 (1973);
23. H. B. Kagan, N. Langlois, and Tuan Phat Dang, J. Organomet. Chem., 90, 353 (1975).
24. See for example: (a) H. Hart and H. S. Eleuterio, J. Am. Chem. Soc., 76, 516 (1954).
25. H. Hart and H. S. Eleuterio, J. Am. Chem. Soc., 76, 1379 (1954).
26. G. Jaouen and R. Dabard, Tetrahedron Lett., 1015 (1971).
27. W. S. Trahanovsky and R. J. Card, J. Am. Chem. Soc., 94, 2897 (1972).
28. M. Acampora, A. Ceccon, M. Dalfarra, G. Giacometti, and G. Rigatti, J. Chem. Soc., Perkin Trans 2, 483 (1977).
29. R. S. Dickson and P. J. Fraser, Adv. Organomet. Chem., 12, 323 (1974).
30. K. M. Nicholas and R. Pettit, Tetrahedron Lett., 3475 (1971);
31. D. Seyferth and A. Wehman, J. Am. Chem. Soc., 92, 5520 (1970).
32. J. H. Wotiz in “Chemistry of Acetylenes”, E. Viehe, Ed., Marcel Dekker, New York, 1969, 365-424.
33. C. A. L. Mahaffy and P. A. L. Pauson, Inorg. Synth., 19, 154 (1979).
34. D. Seyferth, M. O. Nestle, and A. T. Wehman, J. Am. Chem. Soc., 97, 7417 (1975).
35. E. Downer and J. Kenyon, J. Chem. Soc., 1156 (1939).