A truly multifunctional heterocycle: Iminophosphorane, N,P chelate, and dihydropyridine

Angewandte Chemie - International Edition

Volumn 47, Issue 45, 2008, Pages 8674-8677

  Smith, Dan A ^a   Batsanov, Andrei S ^a   Miqueu, Karinne ^b   Sotiropoulos, Jean Marc ^b   Apperley, David C ^a   Howard, Judith A K ^a   Dyer, Philip W ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITÉ DE PAU ET DES PAYS DE L'ADOUR   (France)

Author keywords

Coordination modes; Cycloaddition; Diazaphospholes; Iminophosphoranes; N,P ligands

Indexed keywords

ACETYLENE; CHEMICAL REACTIONS; COORDINATION REACTIONS; LIGHTING; PYRIDINE; RHODIUM;

[2 + 2] CYCLOADDITION; BOND CLEAVAGES; CHEMICAL EQUATIONS; COORDINATION MODES; DIAZAPHOSPHOLES; DIHYDROPYRIDINE; HETEROCYCLE; IMINOPHOSPHORANE; IMINOPHOSPHORANES; MULTI-FUNCTIONAL; N TERMINUSES; N,P LIGANDS; TAUTOMERIC EQUILIBRIUMS; TRIMETHYL ALUMINUMS;

CHEMICAL BONDS;

EID: 55249108489     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200803373     Document Type: Article

References (36)

1. P. Braunstein, F. Naud, Angew. Chem. 2001, 113, 702-722;
2. Angew. Chem. Int. Ed. 2001, 40, 680-699.
3. P. J. Guiry, C. P. Saunders, Adv. Synth. Catal. 2004, 346, 497-537.
4. C. Bianchini, A. Meli, Coord. Chem. Rev. 2002, 225, 35-66.
5. C. Markert, A. Pfaltz, Angew. Chem. 2004, 116, 2552-2554;
6. Angew. Chem. Int. Ed. 2004, 43, 2498-2500.
7. G. Helmchen, A. Pfaltz, Acc. Chem. Res. 2000, 33, 336-345.
8. C. E. Anderson, A. S. Batsanov, P. W. Dyer, J. Fawcett, J. A. K. Howard, Dalton Trans. 2006, 5362-5378.
9. F. Speiser, P. Braunstein, L. Saussine, Acc. Chem. Res. 2005, 38, 784-793.
10. G. Xu, S. R. Gilbertson, Tetrahedron Lett. 2003, 44, 953-955.
11. P. W. Dyer, J. Fawcett, M. J. Hanton, J. Organomet. Chem. 2005, 690, 5264-5281.
12. P. W. Dyer, J. Fawcett, M. J. Hanton, R. D. W. Kemmitt, R. Padda, N. Singh, Dalton Trans. 2003, 104-113.
13. R. B. King, N. D. Sadanani, Synth. React. Inorg. Met.-Org. Chem. 1985, 15, 149-153.
14. A. Maraval, K. Owsianik, D. Arquier, A. Igau, Y. Coppel, B. Donnadieu, M. Zablocka, J.-P. Majoral, Eur. J. Inorg. Chem. 2003, 960-968.
15. Notably, similar ratios of 3o/3c were obtained upon dissolving crystals of 3c in a variety of chlorinated, ethereal, or hydrocarbon solvents.
16. 31P NMR spectroscopy and gave rise to two resonances at δ = +70.3 and +42.0 ppm in a 1:99 ratio, respectively. This is consistent with the 3o/3c equilibrium that exists in solution.
17. See the Supporting Information for details.
18. CCDC 686754 (3c), 686755 (6), and 686756 (7) contain 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.
19. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, Supplement, S1-S18.
20. S. Berger, S. Braun, H.-O. Kalinowski, NMR-Spektroskopie von Nichtmetallen, Georg Thieme, Stuttgart, 1993.
21. -1) were determined and are consistent with facile cyclization/ring-opening processes that favor the closed heterocycle 3c at 298 K.
22. K. T. K. Chan, L. P. Spencer, J. D. Masuda, J. S. J. McCahill, P. Wei, D. W. Stephan, Organometallics 2004, 23, 381-390.
23. C. Freund, N. Barros, H. Gornitzka, B. Martin-Vaca, L. Maron, D. Bourissou, Organometallics 2006, 25, 4927-4930.
24. N. Burford, R. E. v. H. Spence, J. F. Richardson, J. Chem. Soc. Dalton Trans. 1991, 1615-1619.
25. Y. G. Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353-1406.
26. R. M. Acheson, G. Paglietti, P. A. Tasker, J. Chem. Soc. Perkin Trans. 1 1974, 2496-2500.
27. D. A. Smith, P. W. Dyer, unpublished results.
28. S. Green, C. Jones, G. Jin, A. Stasch, Inorg. Chem. 2007, 46, 8-10.
29. T. R. van den Ancker, P. C. Andrews, S. J. King, J. E. McGrady, C. L. Raston, B. A. Roberts, B. W. Skelton, A. H. White, J. Organomet. Chem. 2000, 607, 213-221.
30. L. Baiget, A. S. Batsanov, P. W. Dyer, M. A. Fox, M. J. Hanton, J. A. K. Howard, P. K. Lane, S. A. Solomon, Dalton Trans. 2008, 1043-1054.
31. [15]
32. R. W. Reed, G. Bertrand in Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis (Eds.: L. D. Quin, J. D. Verkade), VCH, New York, 1994, chap. 15, pp. 189-200.
33. See, for example: C. Buron, H. Gornitzka, V. Romanenko, G. Bertrand, Science 2000, 288, 834-836;
34. S. Marrot, T. Kato, F. P. Cossio, H. Gornitzka, A. Baceiredo, Angew. Chem. 2006, 118, 7607-7610;
35. Angew. Chem. Int. Ed. 2006, 45, 7447-7450;
36. P. W. Dyer, J. Fawcett, M. J. Hanton, D. M. Mingos, A.-M. Williamson, Dalton Trans. 2004, 2400-2401.