Convenient room-temperature, mercury-assisted ynthesis of tetrazoles by 1,3-dipolar cycloaddition

European Journal of Inorganic Chemistry

Volumn , Issue 3, 2011, Pages 422-428

  Klapötke, Thomas M ^a   Krumm, Burkhard ^a   Moll, Richard ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Crystal structure; Cycloaddition; Mercury; NMR spectroscopy; Tetrazole

Indexed keywords

CATALYSTS; MASS SPECTROMETRY; MERCURY (METAL); NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

3-DIPOLAR CYCLOADDITION; CRYSTALS STRUCTURES; CYCLOADDITIONS; MERCURY; NMR-SPECTROSCOPY; ORGANOMERCURY; ORGANONITRILES; REGIO-SELECTIVE; TETRAZOLES; ]+ CATALYST;

CRYSTAL STRUCTURE;

EID: 78651440373     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201001046     Document Type: Article

References (50)

1. A. Hantzsch, A. Vagt, Liebig's Ann. 1901, 314, 339-369.
2. J. v. Braun, W. Keller, Ber. Dtsch. Chem. Ges. 1932, 65, 1677-1680.
3. R. Huisgen, Proc. Chem. Soc. London 1961, 357-396.
4. R. Huisgen, Angew. Chem. 1963, 75, 604-637;
5. Angew. Chem. Int. Ed. Engl. 1963, 2, 565 -598.
6. R. Huisgen, The Adventure Playground of Mechanisms and Novel Reactions (Profiles, Pathways, and Dreams. Autobiographies of Eminent Chemists), American Chemical Society, Washington, D. C., 1994.
7. J. I. Seeman, Helv. Chim. Acta 2005, 88, 1145-1153.
8. R. Huisgen, Angew. Chem. 1963, 75, 742-754;
9. Angew. Chem. Int. Ed. Engl. 1963, 2, 633 -645.
10. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004 -2021.
11. Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945-7950.
12. Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2214-2217; Angew. Chem. Int. Ed. 2002, 41, 2110 -2113.
13. F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983-9987.
14. Z. P. Demko, K. B. Sharpless, Angew. Chem. 2002, 114, 2217-2220; Angew. Chem. Int. Ed. 2002, 41, 2113 -2116.
15. A. Padwa, "1,3-Dipolar Cycloaddition Chemistry" in General Heterocyclic Chemistry Series (Eds.:, E. C. Taylor, A. Weissberger), John Wiley & Sons, Inc., New York, 1984.
16. A. Padwa, W. H. Pearson, "Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products" in The Chemistry of Heterocyclic Compounds (Eds.:, E. C. Taylor, P. Wipf, A. Weissberger), John Wiley & Sons, Inc., New York, 2002.
17. P. K. Kadaba, Synthesis 1973, 71-84.
18. W. G. Finnegan, R. A. Henry, R. Lofquist, J. Am. Chem. Soc. 1958, 80, 3908-3911.
19. W. R. Carpenter, J. Org. Chem. 1962, 27, 2085-2088.
20. W. P. Norris, J. Org. Chem. 1962, 27, 3248-3251.
21. Z. P. Demko, K. B. Sharpless, Org. Lett. 2002, 4, 2525-2527.
22. S. Kamijo, T. Jin, Y. Yamamoto, J. Org. Chem. 2002, 67, 7413-7417.
23. I. F. Clemencon, B. Ganem, Tetrahedron 2007, 63, 8665-8669.
24. M. Aldhoun, A. Massi, A. Dondoni, J. Org. Chem. 2008, 73, 9565-9575.
25. T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Chem. Asian J. 2008, 3, 1575-1580.
26. T. Jin, F. Kitahara, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 2008, 49, 2824-2827.
27. V. Aureggi, G. Sedelmeier, Angew. Chem. 2007, 119, 8592-8596; Angew. Chem. Int. Ed. 2007, 46, 8440 -8444.
28. Y. Qiu, B. Liu, G. Peng, J. Cai, H. Deng, M. Zeller, Inorg. Chem. Commun. 2010, 13, 749-752.
29. R. N. Butler, D. P. Shelly, J. Chem. Soc. Perkin Trans. 1 1986, 1101-1105.
30. S. N. Semenov, A. Y. Rogachev, S. V. Eliseeva, Y. A. Belousov, A. A. Drozdov, S. I. Troyanov, Polyhedron 2007, 26, 4899-4907.
31. C. Schilling, N. Jung, S. Bräse, Cycloaddition Reactions with Azides: An Overview in Organic Azides-Syntheses and Applications (Eds.:, S. Bräse, K. Banert), John Wiley & Sons, Ltd., Chichester, 2010, pp. 269-284.
32. D. H. Ess, G. O. Jones, K. N. Houk, Adv. Synth. Catal. 2006, 348, 2337-2361.
33. F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2002, 124, 12210-12216.
34. T. M. Klapötke, B. Krumm, R. Moll, Z. Anorg. Allg. Chem. 2011,.
35. A. J. Brown, O. W. Howarth, P. Moore, J. Chem. Soc., Dalton Trans. 1976, 1589-1592.
36. N. K. Wilson, R. D. Zehr, P. D. Ellis, J. Magn. Reson. 1976, 21, 437-443.
37. G. E. Maciel, M. Borzo, J. Magn. Reson. 1973, 10, 388-390.
38. M. A. Sens, N. K. Wilson, P. D. Ellis, J. D. Odom, J. Magn. Reson. 1975, 19, 323-336.
39. E. Michel, J. Perie, A. Lattes, J. Organomet. Chem. 1981, 204, 1-12.
40. G. A. Webb, Annual Reports on NMR Spectroscopy, Academic Press Inc., London, 1992.
41. S. Poturovic, D. Lu, M. J. Heeg, C. H. Winter, Polyhedron 2008, 27, 3280-3286.
42. K. Dehnicke, D. Seybold, J. Organomet. Chem. 1968, 11, 227-241.
43. J. Lorberth, F. Weller, J. Organomet. Chem. 1971, 32, 145-160.
44. P. L. Goggin, D. M. McEwan, J. Chem. Res. (S) 1978, 171.
45. D. Grdenić, Quart. Rev. 1965, 19, 303-328.
46. A. Bondi, J. Phys. Chem. 1964, 68, 441-451.
47. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, M. C. Burla, G. Polidori, M. Camalli, R. Spagna, SIR97, 1997.
48. A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.
49. G. M. Sheldrick, SHELX-97, University of Göttingen, Göttingen, Germany, 1997.
50. G. M. Sheldrick, Acta Crystallogr., Sect. A 2008, 64, 112-122.