N-Phosphino- and N-Phosphonionitrilimines: From Nucleophilic to Electrophilic 1,3-Dipoles

Journal of Organic Chemistry

Volumn 62, Issue 2, 1997, Pages 292-296

  Palacios, Francisco ^a   Pagalday, Jaione ^a   Piquet, Valérie ^b   Dahan, Françoise ^b   Baceiredo, Antoine ^b   Bertrand, Guy ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000441503     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961443h     Document Type: Article

References (41)

1. For an excellent review, see: Elguero, J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Potts, K. T., Eds.; Pergamon: Oxford, 1984; Vol. 5, p 167.
2. For reviews, see: Kafarski, P.; Lejezak, B. Phosphorus Sulfur 1991, 63, 193. Hoagland, R. E. In Biologically Active Natural Products; Culter, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington DC, 1988; p 182. Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Every Day Living; American Chemical Society: Washington DC, 1987; p 333. Dhawar, D.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
3. For reviews, see: Kafarski, P.; Lejezak, B. Phosphorus Sulfur 1991, 63, 193. Hoagland, R. E. In Biologically Active Natural Products; Culter, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington DC, 1988; p 182. Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Every Day Living; American Chemical Society: Washington DC, 1987; p 333. Dhawar, D.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
4. For reviews, see: Kafarski, P.; Lejezak, B. Phosphorus Sulfur 1991, 63, 193. Hoagland, R. E. In Biologically Active Natural Products; Culter, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington DC, 1988; p 182. Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Every Day Living; American Chemical Society: Washington DC, 1987; p 333. Dhawar, D.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
5. For reviews, see: Kafarski, P.; Lejezak, B. Phosphorus Sulfur 1991, 63, 193. Hoagland, R. E. In Biologically Active Natural Products; Culter, H. G., Ed.; ACS Symposium Series 380; American Chemical Society: Washington DC, 1988; p 182. Toy, A. D. F.; Walsh, E. N. In Phosphorus Chemistry in Every Day Living; American Chemical Society: Washington DC, 1987; p 333. Dhawar, D.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
6. Büchel, K. M. In Protection of Plants and Pest Control; G. Thieme Verlag: Stuttgart, 1977. Tomlin, G., Ed. In The Pesticide Manual, 10th ed.; British Group Protection Pub.: Surrey, 1991. Takaishi, H.; Nakao, I.; Hamaguchi, H. Jpn. Kokai Tokkyo Koho, JP 06 73, 015, 1994; Chem. Abstr. 1994, 121, 108779s.
7. Büchel, K. M. In Protection of Plants and Pest Control; G. Thieme Verlag: Stuttgart, 1977. Tomlin, G., Ed. In The Pesticide Manual, 10th ed.; British Group Protection Pub.: Surrey, 1991. Takaishi, H.; Nakao, I.; Hamaguchi, H. Jpn. Kokai Tokkyo Koho, JP 06 73, 015, 1994; Chem. Abstr. 1994, 121, 108779s.
8. Büchel, K. M. In Protection of Plants and Pest Control; G. Thieme Verlag: Stuttgart, 1977. Tomlin, G., Ed. In The Pesticide Manual, 10th ed.; British Group Protection Pub.: Surrey, 1991. Takaishi, H.; Nakao, I.; Hamaguchi, H. Jpn. Kokai Tokkyo Koho, JP 06 73, 015, 1994; Chem. Abstr. 1994, 121, 108779s.
9. Büchel, K. M. In Protection of Plants and Pest Control; G. Thieme Verlag: Stuttgart, 1977. Tomlin, G., Ed. In The Pesticide Manual, 10th ed.; British Group Protection Pub.: Surrey, 1991. Takaishi, H.; Nakao, I.; Hamaguchi, H. Jpn. Kokai Tokkyo Koho, JP 06 73, 015, 1994; Chem. Abstr. 1994, 121, 108779s.
10. Burchill, R. T.; Cook, M. E. Plant Pathol. 1975, 24, 194.
11. Fest, C.; Riebel, H. J.; Santel, H. J.; Luerssen, K.; Smith, R. R.; Erdelen, Ch.; Hartwig, J.; Turberg, A. Ger. Offen. DE 4, 315, 384, 1994; Chem. Abstr. 1994, 121, 9701d.
12. Fest, C.; Riebel, H. J.; Santel, H. J.; Luerssen, K.; Smith, R. R.; Erdelen, Ch.; Hartwig, J.; Turberg, A. Ger. Offen. DE 4, 315, 384, 1994; Chem. Abstr. 1994, 121, 9701d.
13. Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, Chapter 3, p 291.
14. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565. Huisgen, R.; Palacios, F. Tetrahedron Lett. 1982, 23, 55.
15. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565. Huisgen, R.; Palacios, F. Tetrahedron Lett. 1982, 23, 55.
16. Bertrand, G.; Wentrup, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 527.
17. Sustmann, R. Pure Appl. Chem. 1974, 40, 569.
18. (a) Sicard, G.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1988, 110, 2663.
19. (b) Granier, M.; Baceiredo, A.; Dartiguenave, Y.; Dartiguenave, M.; Menu, M. J.; Bertrand, G. J. Am. Chem. Soc. 1990, 112, 6277.
20. (a) Granier, M.; Baceiredo, A.; Nieger, M.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 1123.
21. (b) Granier, M.; Baceiredo, A.; Bertrand, G.; Huch, V.; Veith, M. Inorg. Chem. 1991, 30, 1161.
22. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4123. Palacios, F.; Alonso, C.; Rubiales, G. Tetrahedron 1995, 51, 3683. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
23. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4123. Palacios, F.; Alonso, C.; Rubiales, G. Tetrahedron 1995, 51, 3683. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
24. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1996, 52, 4123. Palacios, F.; Alonso, C.; Rubiales, G. Tetrahedron 1995, 51, 3683. Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1994, 50, 12727.
25. Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron Lett. 1996, 37, 4577. Palacios, F.; Garcia, J.; Ochoa de Retana, A. M.; Oyarzabal. J. Heterocycl. 1995, 41, 1915.
26. Palacios, F.; Ochoa de Retana, A. M.; Oyarzabal, J. Tetrahedron Lett. 1996, 37, 4577. Palacios, F.; Garcia, J.; Ochoa de Retana, A. M.; Oyarzabal. J. Heterocycl. 1995, 41, 1915.
27. Gilliams, Y.; Smets; G. Makromol. Chem. 1969, 128, 263.
28. Driscoll, J. S.; Hazard, G. F.; Wood, H. B.; Goldin, A. Cancer Chemother. Rep. 1974, 4, 1. Showalter, H. D. H.; Fry, D. W.; Leopold, N. R.; Lown, J. W.; Plambeck, J. A.; Reszka, K. Anti-Cancer Drug Des. 1986, 1, 73.
29. Driscoll, J. S.; Hazard, G. F.; Wood, H. B.; Goldin, A. Cancer Chemother. Rep. 1974, 4, 1. Showalter, H. D. H.; Fry, D. W.; Leopold, N. R.; Lown, J. W.; Plambeck, J. A.; Reszka, K. Anti-Cancer Drug Des. 1986, 1, 73.
30. Wolkoff, P.; Hammerun, S. Acta Chem. Scand. 1976, B30, 837.
31. Barluenga, J.; López, F.; Palacios, F. Tetrahedron Lett. 1987, 28, 2875.
32. Palacios, F.; Pagalday, J.; Ochoa de Retana, A. M. Heterocycles 1995, 40, 543.
33. (a) Sasaki, T.; Hayakawa, K.; Manabe, T.; Nishida, S. J. Am. Chem. Soc. 1981, 103, 565.
34. (b) Taniguchi, H.; Ikeda, T.; Yoshida, Y.; Imoto, E. Bull. Chem. Soc. Jpn. 1977, 50, 2694.
35. (c) Palacios, F.; Pérez de Heredia, I.; Rubiales, G. J. Org. Chem. 1995, 60, 2384.
36. Clavis, J. S.; Fliege, W.; Huisgen, R. Chem. Ber. 1983, 116, 3062. Wentrup, C.; Fischer, S.; Maquestiau, A.; Flammang, R. Angew. Chem., Int. Ed. Engl. 1985, 24, 56. Huisgen, R.; Sustmann, R.; Wallbillich, G. Chem. Ber. 1967, 100, 1786.
37. Clavis, J. S.; Fliege, W.; Huisgen, R. Chem. Ber. 1983, 116, 3062. Wentrup, C.; Fischer, S.; Maquestiau, A.; Flammang, R. Angew. Chem., Int. Ed. Engl. 1985, 24, 56. Huisgen, R.; Sustmann, R.; Wallbillich, G. Chem. Ber. 1967, 100, 1786.
38. Clavis, J. S.; Fliege, W.; Huisgen, R. Chem. Ber. 1983, 116, 3062. Wentrup, C.; Fischer, S.; Maquestiau, A.; Flammang, R. Angew. Chem., Int. Ed. Engl. 1985, 24, 56. Huisgen, R.; Sustmann, R.; Wallbillich, G. Chem. Ber. 1967, 100, 1786.
39. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
40. Sicard, G.; Baceiredo, A.; Crocco, G.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 301.
41. Dubau-Assibat, N.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5216.