Alkylation of Acetonitrile

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8575-8576

  Taber, Douglass F ^a   Kong, Sue ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000039292     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971198h     Document Type: Article

References (11)

1. Julia, M.; Julia, S.; Stalla-Bourdillon, B.; Descoins, C. Bull. Soc. Chim. Fr. 1964, 2533.
2. For previous reports of the direct alkylation of acetonitrile, see: (a) Barrett, G. C.; Grattan, T. J. Tetrahedron Lett. 1979, 4237. (b) Larcheveque, M.; Mulot, P.; Cuvigny, T. J. Organomet. Chem 1973, C33. (c) Horner, L.; Gusten, H. Justus Liebigs Ann. Chem. 1962, 652, 99. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1977, 653. (e) Zhou, S.-E.; Anne, S.; Vandewalle, M. Tetrahedron Lett. 1996, 37, 7637.
3. For previous reports of the direct alkylation of acetonitrile, see: (a) Barrett, G. C.; Grattan, T. J. Tetrahedron Lett. 1979, 4237. (b) Larcheveque, M.; Mulot, P.; Cuvigny, T. J. Organomet. Chem 1973, C33. (c) Horner, L.; Gusten, H. Justus Liebigs Ann. Chem. 1962, 652, 99. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1977, 653. (e) Zhou, S.-E.; Anne, S.; Vandewalle, M. Tetrahedron Lett. 1996, 37, 7637.
4. For previous reports of the direct alkylation of acetonitrile, see: (a) Barrett, G. C.; Grattan, T. J. Tetrahedron Lett. 1979, 4237. (b) Larcheveque, M.; Mulot, P.; Cuvigny, T. J. Organomet. Chem 1973, C33. (c) Horner, L.; Gusten, H. Justus Liebigs Ann. Chem. 1962, 652, 99. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1977, 653. (e) Zhou, S.-E.; Anne, S.; Vandewalle, M. Tetrahedron Lett. 1996, 37, 7637.
5. For previous reports of the direct alkylation of acetonitrile, see: (a) Barrett, G. C.; Grattan, T. J. Tetrahedron Lett. 1979, 4237. (b) Larcheveque, M.; Mulot, P.; Cuvigny, T. J. Organomet. Chem 1973, C33. (c) Horner, L.; Gusten, H. Justus Liebigs Ann. Chem. 1962, 652, 99. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1977, 653. (e) Zhou, S.-E.; Anne, S.; Vandewalle, M. Tetrahedron Lett. 1996, 37, 7637.
6. For previous reports of the direct alkylation of acetonitrile, see: (a) Barrett, G. C.; Grattan, T. J. Tetrahedron Lett. 1979, 4237. (b) Larcheveque, M.; Mulot, P.; Cuvigny, T. J. Organomet. Chem 1973, C33. (c) Horner, L.; Gusten, H. Justus Liebigs Ann. Chem. 1962, 652, 99. (d) Savoia, D.; Trombini, C.; Umani-Ronchi, A. Tetrahedron Lett. 1977, 653. (e) Zhou, S.-E.; Anne, S.; Vandewalle, M. Tetrahedron Lett. 1996, 37, 7637.
7. For a review of nitrile alkylations, see: Arseniyadis, S.; Kyler, K. S; Watt, D. S. Organic Reactions; John Wiley & Sons, Inc.: New York, 1984; Vol. 31, p 1.
8. (a) For the displacement of allylic and benzylic halides with the organocopper derivative of acetonitrile, see: Corey, E. J.; Kuwajima, I. Tetrahedron Lett. 1972, 487. (b) For the displacement of halides, most efficiently allylic and benzylic, with the organozinc derivative of acetonitrile, see: Orsini, F. Synthesis 1985, 500.
9. (a) For the displacement of allylic and benzylic halides with the organocopper derivative of acetonitrile, see: Corey, E. J.; Kuwajima, I. Tetrahedron Lett. 1972, 487. (b) For the displacement of halides, most efficiently allylic and benzylic, with the organozinc derivative of acetonitrile, see: Orsini, F. Synthesis 1985, 500.
10. For general experimental procedures, see: Taber, D. F.; Meagley, R. P.; Doren, D. J. J. Org. Chem. 1996, 61, 5723.
11. Trost, B. M.; Taber, D. F.; Alper, J. B. Tetrahedron Lett. 1976, 3857.