Generation and Reactions of a Selenoamide Dianion

Organic Letters

Volumn 4, Issue 8, 2002, Pages 1407-1409

  Murai, Toshiaki ^a   Aso, Hideo ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

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ARTICLE;

EID: 0012975508     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257629     Document Type: Article

References (38)

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25. For recent examples of the syntheses of selenoamides, see: (a) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647-650. (b) Li, G. M.; Zingaro, R. A. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 136-138, 525-530. (c) Ishihara, H.; Yosimura, K.; Kouketsu, M. Chem. Lett. 1998, 1287-1288. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099-4101. (e) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408-8409.
26. For recent examples of the syntheses of selenoamides, see: (a) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647-650. (b) Li, G. M.; Zingaro, R. A. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 136-138, 525-530. (c) Ishihara, H.; Yosimura, K.; Kouketsu, M. Chem. Lett. 1998, 1287-1288. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099-4101. (e) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408-8409.
27. For recent examples of the syntheses of selenoamides, see: (a) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647-650. (b) Li, G. M.; Zingaro, R. A. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 136-138, 525-530. (c) Ishihara, H.; Yosimura, K.; Kouketsu, M. Chem. Lett. 1998, 1287-1288. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099-4101. (e) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408-8409.
28. For recent examples of the syntheses of selenoamides, see: (a) Li, G. M.; Zingaro, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 647-650. (b) Li, G. M.; Zingaro, R. A. Phosphorus, Sulfur Silicon Relat. Elem. 1998, 136-138, 525-530. (c) Ishihara, H.; Yosimura, K.; Kouketsu, M. Chem. Lett. 1998, 1287-1288. (d) Koketsu, M.; Kanoh, M.; Itoh, E.; Ishihara, H. J. Org. Chem. 2001, 66, 4099-4101. (e) Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408-8409.
29. -1, T = 193 K, R = 0.038, Rw = 0.039, 2921 reflections (I > 3 σ(I)), GOF = 1.65.
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35. Very recently, C-H⋯Se=C and N-H⋯Se=C interactions have been studied: (a) Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, 1125-1126. (b) Wu, R.; Hernández, G.; Dunlap, R. B.; Odom, J. D.; Martinez, R. A.; Silks, L. A. Trends. Org. Chem. 1998, 7, 105-114. (c) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. J. Am. Chem. Soc. 2000, 122, 386. (d) Michalczyk, R.; Schmidt, J. G.; Moody, E.; Li, Z.; Wu, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. Angew. Chem., Int. Ed. 2000, 39, 3067-3070.
36. Very recently, C-H⋯Se=C and N-H⋯Se=C interactions have been studied: (a) Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, 1125-1126. (b) Wu, R.; Hernández, G.; Dunlap, R. B.; Odom, J. D.; Martinez, R. A.; Silks, L. A. Trends. Org. Chem. 1998, 7, 105-114. (c) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. J. Am. Chem. Soc. 2000, 122, 386. (d) Michalczyk, R.; Schmidt, J. G.; Moody, E.; Li, Z.; Wu, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. Angew. Chem., Int. Ed. 2000, 39, 3067-3070.
37. Very recently, C-H⋯Se=C and N-H⋯Se=C interactions have been studied: (a) Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, 1125-1126. (b) Wu, R.; Hernández, G.; Dunlap, R. B.; Odom, J. D.; Martinez, R. A.; Silks, L. A. Trends. Org. Chem. 1998, 7, 105-114. (c) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. J. Am. Chem. Soc. 2000, 122, 386. (d) Michalczyk, R.; Schmidt, J. G.; Moody, E.; Li, Z.; Wu, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. Angew. Chem., Int. Ed. 2000, 39, 3067-3070.
38. Very recently, C-H⋯Se=C and N-H⋯Se=C interactions have been studied: (a) Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, 1125-1126. (b) Wu, R.; Hernández, G.; Dunlap, R. B.; Odom, J. D.; Martinez, R. A.; Silks, L. A. Trends. Org. Chem. 1998, 7, 105-114. (c) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. J. Am. Chem. Soc. 2000, 122, 386. (d) Michalczyk, R.; Schmidt, J. G.; Moody, E.; Li, Z.; Wu, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. Angew. Chem., Int. Ed. 2000, 39, 3067-3070.