Tris(trifluoromethanesulfonyl)methide ('triflide') anion: Convenient preparation, X-ray crystal structures, and exceptional catalytic activity as a counterion with ytterbium(III) and scandium(III)

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2910-2913

  Waller, Francis J ^a   Barrett, Anthony G M ^b   Braddock, D Christopher ^b   Ramprasad, Dorai ^a   McKinnell, R Murray ^b   White, Andrew J P ^b   Williams, David J ^b   Ducray, Richard ^b  

^a AIR PRODUCTS AND CHEMICALS INC   (United States)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; LANTHANIDE; SCANDIUM; TRIS(TRIFLUOROMETHANESULFONYL)METHIDE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; MOLECULAR STABILITY; NITRATION; SYNTHESIS; X RAY ANALYSIS;

EID: 0033574495     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9800917     Document Type: Article

References (28)

1. Reviews: (a) Marshman, R. W. Aldrichimica Acta 1995, 28, 77.
2. (b) Kobayashi, S. Synlett 1994, 689.
3. (c) Engberts, J. B. N. F.; Feringa, B. L.; Keller, E.; Otto, S. Recl. Trav. Chim. Pays Bas 1996, 115, 457.
4. Waller, F. J.; Barrett, A. G. M.; Braddock, D. C.; Ramprasad, D. Chem. Commun. 1997, 613.
5. Waller, F. J.; Barrett, A. G. M.; Braddock, D. C.; Ramprasad, D. Tetrahedron Lett. 1998, 39, 1642.
6. Kobayshi, S.; Moriwaki, M.; Hachiya, I. Bull. Chem. Soc. Jpn. 1997, 70, 267 and references therein.
7. For the use of bis(trifluorosulfonylmethane)imide as a alternative counterion in conjunction with lanthanides, see: (a) Kobayashi, H.; Nie, J.; Sonada, T. Chem. Lett. 1995, 307.
8. (b) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171.
9. For the use of perfluorooctanesulfonate see: (c) Hanamoto, T.; Sugimoto, Y.; Jin, Y. Z.; Inanaga, J. Bull. Chem. Soc. Jpn. 1997, 70, 1421.
10. For the use of a sulphonated resin ae a "counterion" see: (d) Yu, L.; Chen, D.; Li, J.; Wang, P. G. J. Org. Chem. 1997, 62, 3575.
11. (a) Waller, F. J.; Ramprasad, D.; Barrett, A. G. M.; Braddock, D. C. Catalysis of Organic Reactions; Herkes, F., Ed.; Marcel Dekker: New York, 1998; p 289.
12. (b) Waller, F. J.; Barrett, A. G. M.; Braddock, D. C.; Ramprasad, D. J. Chem. Soc., Perkin Trans. 1 1999, in press.
13. Turowsky, L.; Seppelt, K. Inorg. Chem. 1988, 27, 2135.
14. Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q.; Sung, K.-S.; DesMarteau, D. D.; Yagupolskii, L. M.; Yagupolskii, Y. L.; Ignat'ev, N. V.; Kondratenko, N. V.; Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047.
15. (a) Dominey, L. A. US Pat. 5273840, 1993.
16. (a) Koch, V. R.; Dominey, L. A.; Nanjundiah, C.; Ondrechen, M. J. J. Electrochem. Soc. 1996, 143, 798.
17. (b) Walker, C. W., Jr.; Cox, J. D.; Salomon, M. J. Electrochem. Soc. 1996, 143, L80.
18. (a) Gramstad, T.; Hazeldine, R. N. J. Chem. Soc. 1956, 173.
19. (b) Hu, L.-Q., DesMarteau, D. D. Inorg. Chem. 1993, 32, 5007.
20. (a) Hendrickson, J. B.; Bair, K. W. J. Org. Chem. 1977, 42, 3875.
21. (b) Hendrickson, J. B.; Sternbach, D. D.; Bair, K. W. Acc. Chem. Res. 1977, 10, 306 and references therein.
22. Triflic anhydride is known to oxidize Grignard reagents: Creary, X. J. Org. Chem. 1980, 45, 2727.
23. (a) Koshar, R. J.; Mitsch, R. A. J. Org. Chem. 1973, 38, 3358.
24. (b) Gramstad, T.; Hazeldine, R. N. J. Chem. Soc. 1957, 4069.
25. Forsberg, J. H.; Spaziano, V. T.; Balasubramanian, T. M.; Liu, G. K.; Kinsley, S. A.; Duckworth, C. A.; Poteruca, J. J.; Brown, P. S.; Miller, J. L. J. Org. Chem. 1987, 52, 1017.
26. Failure to locate the positions of the hydrogen atoms on either the aqua ligands or the included water molecule precluded detailed analysis of the hydrogen bonding geometries. However, there are in the ytterbium complex, for example, some fourteen O...O contacts between the aqua ligands and either the included water molecule or the triflide anions of less than 3 Å.
27. For the interesting use of the triflide counteranion in diazonium salts and their decomposition products, see: (a) Zhu, S.-Z.; DesMarteau, D. D. Inorg. Chem. 1993, 32, 224.
28. (b) Yagupolskii, Y. L.; Pavlenko, N. V.; Yurev, I. I.; Iksanova, S. V. Zh. Org. Khim. 1990, 26, 682.