Cycloaddition of nitrones to free and coordinated (E)-cinnamonitrile: Effect of metal coordination and microwave irradiation on the selectivity of the reaction

Dalton Transactions

Volumn , Issue 12, 2003, Pages 2544-2549

  Desai, Bimbisar ^a   Danks, Timothy N ^a,b   Wagner, Gabriele ^a  

^a UNIVERSITY OF SURREY   (United Kingdom)

^b Oratory School   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; COMPLEXATION; COORDINATION REACTIONS; IRRADIATION; KETONES; MIXTURES; NITROGEN COMPOUNDS; PLATINUM COMPOUNDS;

CYCLOADDITION; HETEROCYCLIC LIGANDS; NITRONES; OXADIAZOLINES;

REACTION KINETICS;

EID: 1642550162     PISSN: 14779226     EISSN: 14779234     Source Type: Journal    
DOI: 10.1039/b302086j     Document Type: Article

References (51)

1. (a) S. Kobayashi and K. A. Jorgensen, Cycloaddition Reactions in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2002;
2. (b) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, UK, 1990.
3. (a) L. F. Tietze and G. Kettschau, Top. Curr. Chem., 1997, 189, 1;
4. (b) H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007;
5. (c) U. Pindur, G. Lutz and C. Otto, Chem. Rev., 1993, 93, 741.
6. (a) R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565;
7. (b) R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 633;
8. (c) 1,3 Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley-Interscience, New York, 1984, vol. 1-2.
9. S. Kanemasa, T. Uemura and E. Wada, Tetrahedron Lett., 1992, 33, 7889.
10. (a) K. V. Gothelf and K. A. Jorgensen, Chem. Commun., 2000, 1449 and references therein;
11. (b) K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 1998, 98, 863.
12. (a) S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 1998, 120, 5840;
13. (b) M. Kawamura and S. Kobayashi, Tetrahdron Lett., 1999, 40, 3213.
14. (a) S. Kanemasa, M. Nishiuchi and A. Kamimura, J. Am. Chem. Soc., 1994, 116, 2324;
15. (b) S. Kanemasa, S. Kobayashi, M. Nishiuchi, H. Yamamoto and E. Wada, Tetrahedron Lett., 1991, 32, 6367.
16. (a) P. Allway and R. Grigg, Tetrahedron Lett., 1991, 32, 5817;
17. (b) R. Grigg, Tetrahedron: Asymmetry, 1995, 6, 2475.
18. (a) G. Wagner and M. Haukka, J. Chem. Soc., Dalton Trans., 2001, 2690;
19. (b) G. Wagner, M. Haukka, J. J. R. Fraústo da Silva, A. J. L. Pombeiro and V. Yu. Kukushkin, Inorg. Chem., 2001, 40, 264;
20. (c) G. Wagner, A. J. L. Pombeiro and V. Yu. Kukushkin, J. Am. Chem. Soc., 2000, 122, 3106.
21. G. Wagner, Chem. Eur. J., 2003, 9, 1503.
22. (a) A. de la Hoz, A. Díaz-Ortiz, A. Moreno and F. Langa, Eur. J. Org. Chem., 2000, 3659;
23. (b) A. de la Hoz, A. Díaz-Ortiz and F. Langa, in Microwaves in Organic Synthesis, ed. A. Loupy, Wiley/VCH, Weinheim, Germany, 2002.
24. L. Perreux and A. Loupy, Tetrahedron, 2001, 57, 9199.
25. (a) A. Díaz-Ortiz, E. Díez-Barra, A. de la Hoz, P. Prieto and A. Moreno, J. Chem. Soc., Perkin Trans. 1, 1994, 3595;
26. (b) H. Kaddar, J. Hamelin and H. Benhaua, J. Chem. Res., 1999, 718;
27. (c) F. Louërat, K. Bougrin, A. Loupy, A. M. Ochoa de Retana, J. Pagalday and F. Palacios, Hetcrocycles, 1998, 48, 161.
28. A. Díaz-Ortiz, E. Díez-Barra, A. de la Hoz, A. Moreno, M. J. Gómez-Escalonilla and A. Loupy, Heterocycles, 1996, 43, 1021.
29. (a) P. Mičúch, L. Fišera, M. K. Cyrański, T. M. Krygowski and J. Krajčik, Tetrahedron, 2000, 56, 5465;
30. (b) P. Micúch, L. Fišera, M. K. Cyranski and T. M. Krygowski, Tetrahedron Lett., 1999, 40, 167;
31. (c) B. Garrigues, R. Laurent, C. Laporte, A. Laporterie and J. Dubac, Liebigs Ann., 1996, 5, 743.
32. (a) K. N. Houk, J. Sims, R. E. Duke, Jr., R. W. Strozier and J. K. George, J. Am. Chem. Soc., 1973, 95, 7287;
33. (b) K. N. Houk, J. Sims, C. R. Watts and L. J. Luskus, J. Am. Chem. Soc., 1973, 95, 7301.
34. R. Sustmann, W. Sicking and R. Huisgen, J. Am. Chem. Soc., 1995, 117, 9679.
35. R. J. Hinkle, P. J. Stang and A. M. Arif, Organometallics, 1993, 12, 3510.
36. E. Costa, P. G. Pringle, M. B. Smith and K. Worboys, J. Chem. Soc., Dalton Trans., 1997, 4277.
37. (a) A. L. Seligson and W. C. Trogler, Organometallics, 1993, 12, 774;
38. (b) K. Y. Yang, R. J. Lachiotte and R. Eisenberg, Organometallics, 1998, 17, 5102;
39. (c) D. K. Wicht, I. Kovacik, D. S. Glueck, L. M. Liable-Sands, C. D. Incarvito and A. L. Rheingold, Organometallics, 1999, 18, 5141;
40. (d) J. M. Seul and S. Park, J. Chem. Soc., Dalton Trans., 2002, 1153.
41. M. Bolte, M. Massaux and J. Zarembowitch, Transition Met. Chem., 1984, 9, 461.
42. F. D. Rochon, R. Melanson, E. Thouin, A. L. Beauchamp and C. Bensimon, Can. J. Chem., 1996, 74, 144.
43. (a) M. Burdisso, R. Gandolfi and P. Grunanger, Tetrahedron, 1989, 45, 5579;
44. (b) R. Grigg, M. Jordan, A. Tangthongkum, F. W. B. Einstein and T. Jones, J. Chem. Soc., Perkin Trans. 1, 1984, 47.
45. (a) A. Corsaro, U. Chiacchio, G. Perrini, P. Caramello and G. Purello, J. Chem. Res. (S), 1984, 402;
46. (b) A. Corsaro, U. Chiacchio, A. Compagnini and G. Purello, J. Chem. Soc., Perkin Trans. 1, 1980, 1635;
47. (c) A. Corsaro, U. Chiacchio and G. Purello, J. Chem. Soc., Perkin Trans. 1, 1977, 2154.
48. M. Joucla, D. Grée and J. Hamelin, Tetrahedron, 1973, 29, 2315.
49. (a) F. P. Fanizzi, F. P. Intini, L. Maresca and G. Natile, J. Chem. Soc., Dalton Trans., 1990, 199;
50. (b) K. A. Hoffmann and G. Bugge, Chem. Ber., 1907, 40, 1772.
51. Houben-Weyl, Methoden der Organischen Chemie, 4 Aufl., Vol. E14b, Thieme Verlag, Stuttgart, Germany, 1990.