Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H)

Organometallics

Volumn 17, Issue 2, 1998, Pages 146-150

  Nudelman, Norma Sbarbati ^a   Schulz, Hernan ^a   Liñares, Guadalupe García ^a   Bonatti, Alejandro ^a   Boche, Gernot ^b  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001167743     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970293d     Document Type: Article

References (32)

1. For reviews of structural studies of N-lithiated species, see: (a) Gregory, K.; Schleyer, P. v. R.; Snaith, R. Adv. Inorg. Chem. 1991, 37, 47.
2. (b) Mulvey, R. E. Chem. Soc. Rev. 1991, 20, 167.
3. Nudelman, N. S. Carbonylation of Main-Group Organometal Compounds In The Chemistry of Double Bonded Functional Groups; Patai, S., Ed.; Wiley, Chichester, 1989.
4. Collum, D. B. Acc. Chem. Res. 1993, 26, 227.
5. Nichols, M. A.; Waldmüller, D.; Williard, P. G. J. Am. Chem. Soc. 1994, 116, 1153.
6. Nudelman, N. S.; Lewkowicz, E. S.; Furlong, J. J. P. J. Org. Chem. 1993, 58, 1847.
7. (a) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863.
8. (b) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1994, 116, 6009.
9. Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217.
10. Nudelman, N. S.; Lewkowicz, E. S.; Perez, D. G. Synthesis 1990, 10, 917.
11. Vedejs, E.; Lee, N. J. Am. Chem. Soc. 1995, 117, 891 and previous references.
12. Boche, G.; Langlotz, I.; Marsch, M.; Harms, K.; Nudelman, N. S. Angew. Chem., Int. Ed. Engl. 1992, 104, 774.
13. (a) Pérez, D. G.; Nudelman, N. S. J. Org. Chem. 1988, 53, 408.
14. (b) Pérez, D. G.; Nudelman, N. S. J. Org. Chem. 1983, 48, 133.
15. Bitsi, G.; Jenner, G. J. Organomet. Chem. 1987, 330 (3), 429.
16. Nudelman, N. S.; García Liñares, G.; Schulz, H. Main Group Met. Chem. 1995, 78, 147.
17. (a) Nudelman, N. S.; Doctorovich, F.; García Liñares, G.; Schulz, H. Gazz. Chim. Ital. 1996, 126, 19.
18. (b) Nudelman, N. S.; García Liñares, G. An. Asoc. Quim. Argent. 1996, 619.
19. Murugan, R.; Scriven, E. F.; Zhang, T. Y. PCT Int. Appl. WO 95 15,313, 1995; Chem. Abstr. 123, 143654k.
20. Packman, T. W.; Germain, A. L.; Patel, R.; Barras, J. R.; Milne, D. J. PCT Int. Appl. WO 95 07,877, 1995; Chem. Abstr. 1995, 123, 55483y.
21. Faraj, M. K. U.S. Patent 5,155,267, 1992; Chem. Abstr. 118, 80639h.
22. Koeckritz, P.; Liebscher, J.; Schmidt, L. German (East) Patent DD 241,073, 1986; Chem. Abstr. 1986, 107, 96347v.
23. Patschorke, J. Patentschrift (Switz.) CH 657,862, 1986; Chem. Abstr. 1986, 106, 70316p.
24. Dahbi, T. P.; Shah, V. H.; Parikh, A. R. Indian J. Heterocycl. Chem. 1992, 2 (2), 137.
25. Waver, I.; Osek, J. J. Chem. Soc., Perkin Trans. 2 1985, 1669.
26. Furlong, J. J. P.; Lewkowicz, E. S.; Nudelman, N. S. J. Chem. Soc., Perkin Trans.2 1990, 1461.
27. Fraenkel, G.; Subramanian, S.; Chow, A. J. Am. Chem. Soc. 1995, 117, 6300.
28. We thank one of the referees for this comment.
29. Viruela-Martin, P.; Viruela-Martin, R.; Tomas, F.; Nudelman, N. S. J. Am. Chem. Soc. 1994, 116, 10110.
30. 13C NMR module was developed by Dr Ernö Pretsch of the Department of Organic Chemistry, ETH, Zurich, Switzerland.
31. Majewski, M.; Gleave, D. M. J. Organomet. Chem. 1994, 470, 1.
32. Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sensitive Compounds, 2nd ed.; Wiley: New York, 1986.