Activation of the C-F bond: Transformation of CF3N=N- into 5-azidotetrazoles

Angewandte Chemie - International Edition

Volumn 47, Issue 37, 2008, Pages 7087-7090

  Abe, Takashi ^a   Tao, Guo Hong ^a   Joo, Young Hyuk ^a   Huang, Yangen ^a   Twamley, Brendan ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

Azo compounds; C F activation; Hydrazones; Nitrogen heterocycles; Tetrazoles

Indexed keywords

EID: 54749136530     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802459     Document Type: Article

References (39)

1. a) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. 2006, 118, 3664-3682;
2. Angew. Chem. Int. Ed. 2006, 45, 3584-3601;
3. b) G. Steinhauser, T. M. Klapötke, Angew. Chem. 2008, 120, 3376-3394;
4. Angew. Chem. Int. Ed. 2008, 47, 3330-3347;
5. c) R. P. Singh, H. Gao, D. T. Meshri, J. M. Shreeve in High Energy Density Materials (Ed.: T. M. Klapötke), Springer, Heidelberg, 2007, pp. 35-83;
6. d) T. M. Klapötke in High Energy Density Materials (Ed.: T. M. Klapötke), Springer, Heidelberg, 2007, pp. 85-122;
7. e) R. N. Butler in Comprehensive Heterocyclic Chemistry II. A review of the literature 1982-1985, Vol. 4 (Eds.: A. R. Katritzky, C. W. Rees, E. F. Scriven), Pergamon, New York, 1996, pp. 897-904.
8. a) J. C. Kauer, W. A. Sheppard, J. Org. Chem. 1967, 32, 3580-3592;
9. b) J. A. C. Alves, R. A. W. Johnstone, Synth. Commun. 1997, 27, 2645-2650.
10. W. Friderich, K. Flick, US 2179783, 1939 [Chem. Abstr. 1940, 34, 11610].
11. a) A. Hammerl, T. M. Klapötke, Inorg. Chem. 2002, 41, 906-912;
12. b) A. Hammerl, T. M. Klapötke,H. Nöth, M. Warchhold, G. Holl, Propellants Explos. Pyrotech. 2003, 28, 165-173;
13. c) A. Hammerl, T. M. Klapötke, P. Mayer, J. J. Weigand, Propellants Explos. Pyrotech. 2005, 30, 17-26;
14. d) J. Stierstorfer, T. M. Klapötke, A. Hammerl, R. D. Chapman, Z. Anorg. Allg. Chem. 2008, 634, 1051-1057.
15. a) A. H. Dinwoodie, R. N. Haszeldine, J. Chem. Soc. 1965, 2266-2268;
16. b) S. P. Makarov, A. S. Filatov, A. Ya. Yakubovich, Zh. Obshch. Khim. 1967, 37, 158-163;
17. c) A. S. Filatov, S. P. Makarov, A. Ya. Yakubovich, Zh. Obshch. Khim. 1967, 37, 837-841;
18. d) S. P. Makarov, A. Ya. Yakubovich, A. S. Filatov, M. A. Lnglin, T. Ya. Nikiforova, Zh. Obshch. Khim. 1968, 38, 709-715;
19. e) G. Bolte, A. Haas, J. Fluorine Chem. 1984, 26, 69-76;
20. f) P. Gölitz, A. de Meijere, Angew. Chem. 1981, 93, 302-303;
21. g) K. Charavorty, J. M. Pearson, M. J. Szearc, J. Phys. Chem. 1969, 73, 746-748;
22. h) P. S. Engel, W.-X. Wu, J. Org. Chem. 1990, 55, 1503-1505;
23. i) A. Sekiya, T. Umemoto, Chem. Lett. 1982, 1519;
24. j) A. Sekiya, T. Umemoto, Bull. Chem. Soc. Jpn. 1984, 57, 2962-2964.
25. V. A. Ginsburg, A. Ya. Yakubovich, A. S. Filatov, G. E. Zelenin, S. P. Makarov, V. A. Shpanskii, G. P. Kotel'nikova, L. F. Segienko, L. L. Martynova, Dokl. Akad. Nauk SSSR 1962, 142, 354-357.
26. 3 = 1:2, 25°C/24 h, 75%, 92.4 mg), 2 f (60°C/8 h, 89%, 110 mg), 2g (60°C/8 h, 93%, 139 mg).
27. a) T. Ono, V. P. Kukhar, V. A. Soloshonok, J. Org. Chem. 1996, 61, 6563-6569;
28. b) V. A. Soloshonok, T. Ono, Tetrahedron 1996, 52, 14701-14712;
29. c) V. A. Soloshonok, T. Ono, Synlett 1996, 919-921.
30. A. F. Gonter, E. N. Glatov, A. S. Vinogradov, E. G. Bykhovskaya, I. L. Knunyants, Izv. Akad. Nauk SSSR Ser. Khim. 1985, 700-703.
31. a) G. Köter, K. Seppelt, J. Am. Chem. Soc. 1979, 101, 347-349;
32. b) K. A. Petrov, A. A. Neimysheva, J. Gen. Chem. USSR (Engl. Transl.) 1969, 29, 2135-2139.
33. 19F NMR spectroscopy, as it gives rise to two doublets in the region of δ=-42 to -49 and -56 to -58 ppm.
34. 3CN (2.5 mL), 25°C/24 h, 86% Yield, 18.3 mg.
35. 2 = 0.0790, 134 parameters. CCDC 685655 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
36. a) H. P. Diogo, J. J. Moura, Phase Transitions 2005, 78, 357-368;
37. b) S. Schneider, G. Drake, L. Hall, T. Hawkins, M. Rosander, Z. Anorg. Allg. Chem. 2007, 633, 1701-1707.
38. Gaussian '03 (Revision D.01), M. J. Frisch et al., see Supporting Information.
39. S. Bastea, L. E. Fried, K. R. Glaesemann, W. M. Howard, P. C. Souers, P. A. Vitello, Cheetah 5.0 UserDs Manual, Lawrence Livermore National Laboratory, 2007.