Generation and reaction of metal free trifluoroacetimidoyl carbanion

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 6055-6057

  Uneyama, Kenji ^a   Noritake, Chiemi ^a   Sadamune, Keiji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011229247     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960259t     Document Type: Article

References (31)

1. (a) Filler, R.; Kobayashi, Y. Biomedicinal Aspects of Fluorine Chemistry; Kodansha Ltd.: Tokyo, 1982.
2. (b) Hudlicky, M. Chemistry of Organic Fluorine Compounds; Ellis Horwood: New York, 1976.
3. (c) Ishikawa, N. Fussokagaku no Gousei to Kinou, in Japanese; CMC: Tokyo, 1987.
4. (a) Ishikawa, N. Biologically Active Organofluorine Compounds; CMC: Tokyo, 1990.
5. (b) Welch, J. T. Tetrahedron 1987, 43, 3123.
6. (c) Bravo, P.; Resnati, G. Tetrahedron Asymm. 1990, 1, 661.
7. (d) Resnati, G. Tetrahedron 1993, 49, 9385.
8. Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32.
9. (a) Uneyama, K.; Morimoto, O.; Yamashita, F. Tetrahedron Lett. 1989, 30, 4821.
10. (b) Kobayashi, M.; Sadamune, K.; Mizukami, H.; Uneyama, K. J. Org. Chem. 1994, 59, 1909.
11. (c) Uneyama, K.; Yamashita, F.; Sugimoto, K.; Morimoto, O. Tetrahedron Lett. 1990, 31, 2717.
12. (a) Dan-oh, Y.; Matta, H.; Uemura, J.; Watanabe, H.; Uneyama, K. Bull. Chem. Soc. Jpn. 1995, 68, 1497.
13. (b) Ueda, Y.; Watanabe, H.; Uemura, J.; Uneyama, K. Tetrahedron Lett. 1993, 34, 7933.
14. (a) Uneyama, K.; Watanabe, H. Tetrahedron Lett. 1991, 32, 1459.
15. (b) Watanabe, H.; Hashizume, Y.; Uneyama, K. Ibid. 1992, 33, 4333.
16. Tamura, K.; Yan, F.-Y.; Sakai, T.; Uneyama, K. Bull. Chem. Soc. Jpn. 1994, 67, 300.
17. (a) Watanabe, H.; Yamashita, F.; Uneyama, K. Tetrahedron Lett. 1993, 34, 1941.
18. (b) Watanabe, H.; Yan, F.-Y.; Sakai, T.; Uneyama, K. J. Org. Chem. 1994, 59, 758.
19. The carbene type intermediate has been proposed for benzoyllithium. (a) Trzupek, L. S.; Newirth, T. L.; Kelly, E. G.; Nudelman, N. S.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 8118. (b) Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625. (c) Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534.
20. The carbene type intermediate has been proposed for benzoyllithium. (a) Trzupek, L. S.; Newirth, T. L.; Kelly, E. G.; Nudelman, N. S.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 8118. (b) Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625. (c) Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534.
21. The carbene type intermediate has been proposed for benzoyllithium. (a) Trzupek, L. S.; Newirth, T. L.; Kelly, E. G.; Nudelman, N. S.; Whitesides, G. M. J. Am. Chem. Soc. 1973, 95, 8118. (b) Nudelman, N. S.; Vitale, A. A. J. Org. Chem. 1981, 46, 4625. (c) Seyferth, D.; Weinstein, R. M. J. Am. Chem. Soc. 1982, 104, 5534.
22. Nonfluorinated alkyl and aryl imidoyl metals have been reported. (a) Niznik, G. E.; Morrison, W. H., III; Walborsky, H. M. J. Org. Chem. 1974, 39, 600. (b) Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888. (c) Murakami, M.; Ito, H.; Bakar, W. A. W. A.; Baba, A. B. Chem. Lett. 1989, 1603 and other literatures cited in the references above.
23. Nonfluorinated alkyl and aryl imidoyl metals have been reported. (a) Niznik, G. E.; Morrison, W. H., III; Walborsky, H. M. J. Org. Chem. 1974, 39, 600. (b) Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888. (c) Murakami, M.; Ito, H.; Bakar, W. A. W. A.; Baba, A. B. Chem. Lett. 1989, 1603 and other literatures cited in the references above.
24. Nonfluorinated alkyl and aryl imidoyl metals have been reported. (a) Niznik, G. E.; Morrison, W. H., III; Walborsky, H. M. J. Org. Chem. 1974, 39, 600. (b) Ito, Y.; Matsuura, T.; Murakami, M. J. Am. Chem. Soc. 1987, 109, 7888. (c) Murakami, M.; Ito, H.; Bakar, W. A. W. A.; Baba, A. B. Chem. Lett. 1989, 1603 and other literatures cited in the references above.
25. Methylation and iodination on methylene of 2,2,2-trifluoroethyl phenyl sulfone. Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378.
26. It has been also reported that the quaternary ammonium cation was useful as counter cation for the generation of enolate from α-trifluoromethyl malonates by electrogenerated base. Fuchigami, T.; Nakagawa, Y. J. Org. Chem. 1987, 52, 5276.
27. (a) Capperucci, A.; Degl'Innocenti, A.; Faggi, C.; Ricci, A. J. Org. Chem. 1988, 53, 3612.
28. (b) Bonini, B. F.; Busi, F.; de Laet, R. C.; Mazzanti, G.; Thuring, J.-W. J. F.; Zani, P.; Zwanenburg, B. J. Chem. Soc., Perkin Trans. 1 1993, 1011.
29. 3 with MeLi has been proposed. Hudrlik, P. F.; Waugh, M. A.; Hudrlik, A. M. J. Organomet. Chem. 1984, 271, 69.
30. Determined by GC analysis.
31. 19F NMR analysis of crude reaction mixture after 5 min showed a peak of 145.2 ppm which was also detected in the absence of imidoyltrimethylsilane 10a and almost consistent with that (145.5 ppm) of 2-ethylhexyl fluoroformate.