N-(trifluoromethylsulfonyl)aryloxytrifluoromethylsulfoximines [ArO-SO(CF3)=NTf] and N-aryltriflimides Ar-N(Tf)2 by thermal and photolytic dediazoniation of [ArN2][BF4] in [BMIM][Tf2N] ionic liquid: Exploiting the ambident nucleophilic character of a "nonnucleophilic" anion

Journal of Organic Chemistry

Volumn 72, Issue 18, 2007, Pages 6758-6762

  Laali, Kenneth K ^a   Okazaki, Takao ^a   Bunge, Scott D ^a  

^a KENT STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIDENT NUCLEOPHILES; OXY ANION QUENCHING PRODUCTS; THERMAL DEDIAZONIATION; X RAY STRUCTURE;

ARGON; NEGATIVE IONS; NUCLEOPHILES; PHOTOLYSIS; SOLVENTS; X RAY ANALYSIS;

NITROGEN COMPOUNDS;

1 BUTYL 3 METHYLIMIDAZOLIUM BIS(TRIFLUOROMETHANESULFONATO)AMIDE; BORIC ACID; IMIDAZOLE DERIVATIVE; IONIC LIQUID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFOXIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; EXTRACTION; PHOTOLYSIS; REACTION ANALYSIS; RING CLOSING METATHESIS; ROOM TEMPERATURE; SOLVATION; STRUCTURE ANALYSIS; SYNTHESIS; THERMAL ANALYSIS; X RAY ANALYSIS;

EID: 34548789522     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0708801     Document Type: Article

References (31)

1. Laali, K. K.; Gettwert, V. J. J. Fluorine Chem. 2001, 107, 31-34.
2. Bonhote, P.; Dias, A.-P.; Papageorgiou, N.; Kalyanasundram, K.; Graetzel, M. Inorg. Chem. 1996, 35, 1168-1178.
3. Oldham, W. J., Jr.; Costa, D. A.; Smith, W. H. In Ionic Liquids, Industrial Applications to Green Chemistry; Rogers, R. D., Seddon, K. R., Eds.; ACS Symp. Ser. No. 818; American Chemical Society: Washington, DC, 2002; Chapter 15.
4. Anthony, J. L.; Brennecke, J. F.; Holbery, J. D.; Maginn, E. J.; Mantz, R. A.; Rogers, R. D.; Trulove, P. C.; Visser, A. E.; Welton, T. In Ionic Liquids in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Weinheim, Germany, 2003; Chapter 3.
5. (a) Vij, A.; Kirchmeier, R. L.; Shreeve, J. M.; Verma, R. D. Coord. Chem. Rev. 1997, 158, 413-432.
6. (b) Foropoulos, J., Jr.; DesMarteau, D. D. Inorg. Chem. 1984, 23, 3720-3723.
7. Mudring, A.-V.; Babai, A.; Arenz, S.; Giernoth, R. Angew. Chem., Int. Ed. 2005, 44, 5485-5488.
8. Bini, R.; Bortolini, O.; Chiappe, C.; Pieraccini, D.; Siciliano, T. J. Phys. Chem. B 2007, 111, 598-604.
9. Bini, R.; Chiappe, C.; Marmugi, E.; Pieraccini, D. Chem. Commun. 2006, 897-899.
10. Haas, A.; Yagupol'skii, Y. L.; Klare, C. Mendeleev Commun. 1992, 70.
11. Zhu, S.-Z.; DesMarteau, D. D. Inorg. Chem. 1993, 32, 223-226.
12. (a) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 4607-4610.
13. (b) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 3839-3842.
14. (c) Gandel'sman, L. Z.; Dronkina, M. I.; Nazaretyan, V. P.; Yagupol'skii, L. M. Zh. Org. Khim. 1972, 8, 1659-1662; CA 77:139555.
15. (d) Yagupol'skii, L. M.; Gandel'sman, L. Z.; Nazaretyan, V. P. Zh. Org. Khim. 1974, 10, 889-890; CA 81:25298.
16. (e) Gandel'sman, L. Z.; Yagupol'skii, L. M. Ukr. Khim. Zh. 1975, 41, 640-642; CA 83:78784.
17. Sarca, V. D.; Laali, K. K. Green Chem. 2006, 8, 615-620.
18. Laali, K. K.; Sarca, V. D.; Okazaki, T.; Brock, A.; Der, P. Org. Biomol. Chem. 2005, 3, 1034-1042.
19. Sarca, V. D.; Laali, K. K. Green. Chem. 2004, 6, 245-248.
20. Laali, K. K.; Borodkin, G. I. J. Chem. Soc., Perkin Trans. 2 2002, 953-957.
21. Laali, K. K.; Gettwert, V. J. J. Org. Chem. 2001, 66, 35-40.
22. Laali, K. K. In Ionic Liquids in Organic Synthesis; ACS Symp. Ser, No. 950; Malhotra, S. V., Ed.; American Chemical Society: Washington, DC, 2007; pp 16-27.
23. Zollinger, H. In Diazo Chemistry I; VCH: Weinheim, Germany, 1994; Chapter 8.
24. See Chapter 10 in ref 18.
25. (a) Shainyan, B. A.; Tolstikov, L. L.; Zhinkin, A. R. Russ. J. Org. Chem. 2003, 39, 1180-1182.
26. (b) Dantzig, A. H.; Grese, T. A.; Norman, B. H.; Palkowitz, A. D.; Sluka, J. P.; Starling, J. J.; Winter, M. A. EP 773217; CA 127:50535.
27. 1H FT NMR spectra; Aldrich Chemical Co.: Milwaukee, WI, 1993.
28. (b) Stavber, S.; Zupan, M. J. Org. Chem. 1985, 50, 3609-3612.
29. (c) Stavber, S.; Zupan, M. J. Org. Chem. 1983, 48, 2223-2226.
30. (d) Laali, K. K.; Borodkin, G. L. J. Chem. Soc., Perkin Trans. 2 2002, 953-957.
31. Krossing, I.; Slattery, J. M.; Daguenet, C.; Dyson, P. J.; Oleinikova, A.; Weingärter, H. J. Am. Chem. Soc. 2006, 128, 13427-13434.