Remarkable metal-complexed phosphorus analogues of the cyclopropenylcarbene-cyclobutadiene rearrangement

Journal of the American Chemical Society

Volumn 133, Issue 25, 2011, Pages 9704-9707

  Lyaskovskyy, Volodymyr ^a   Elders, Niels ^a   Ehlers, Andreas W ^a   Lutz, Martin ^b   Slootweg, J Chris ^a   Lammertsma, Koop ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTADIENES; REACTION PATHWAYS; STRUCTURAL CHANGE; TRICARBONYL COMPLEXES; VALENCE ISOMER;

CARBON MONOXIDE; CARBONYLATION; IRON COMPOUNDS; ISOMERS; PHOSPHORUS;

BUTADIENE;

CARBON MONOXIDE; CHEMICAL COMPOUND; CYCLOBUTADIENE; CYCLOPROPENYLCARBENE; METAL COMPLEX; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ALLYLIC REARRANGEMENT; ARTICLE; CHEMICAL BINDING; DENSITY FUNCTIONAL THEORY; FRAGMENTATION REACTION; ISOMERIZATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE;

BUTADIENES; COORDINATION COMPLEXES; CYCLOBUTANES; CYCLOPROPANES; METHANE; ORGANIC CHEMISTRY PROCESSES; PHOSPHINES; PHOSPHORUS;

EID: 79959512390     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja203083c     Document Type: Article

References (46)

1. Maier, G. Angew. Chem., Int. Ed. Engl. 1974, 13, 425-438
2. Bally, T.; Masamune, S. Tetrahedron 1980, 36, 343-370
3. Cram, D. J.; Tanner, M. E.; Thomas, R. Angew. Chem., Int. Ed. Engl. 1991, 30, 1024-1027
4. Maier, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 309-332
5. Maier, G.; Neudert, J.; Wolf, O.; Pappusch, D.; Sekiguchi, A.; Tanaka, M.; Matsuo, T. J. Am. Chem. Soc. 2002, 124, 13819-13826
6. Emerson, G. F.; Watts, L.; Pettit, R. J. Am. Chem. Soc. 1965, 87, 131-133
7. Seyferth, D. Organometallics 2003, 22, 2-20
8. Closs, G. L.; Rao, V. N. M. J. Am. Chem. Soc. 1966, 88, 4116-4117
9. Maier, G.; Neudert, J.; Wolf, O. Angew. Chem., Int. Ed. 2001, 40, 1674-1675
10. Masamune, S.; Nakamura, N.; Suda, M.; Ona, H. J. Am. Chem. Soc. 1973, 95, 8481-8483
11. Wingert, H.; Regitz, M. Chem. Ber. 1986, 119, 244-256
12. Fink, M. J.; Puranik, D. B.; Johnson, M. P. J. Am. Chem. Soc. 1988, 110, 1315-1316
13. Puranik, D. B.; Fink, M. J. J. Am. Chem. Soc. 1989, 111, 5951-5952
14. Vogelbacher, U.-J.; Regitz, M.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1986, 25, 842-843
15. Ledermann, M.; Regitz, M.; Angermund, K.; Binger, P.; Krüger, C.; Mynott, R.; Gleiter, R.; Hyla-Kryspin, I. Angew. Chem., Int. Ed. Engl. 1988, 27, 1559-1562
16. 2-Phosphino-2 H -phosphirenes undergo a similar ring-expansion reaction. See: Sanchez, M.; Réau, R.; Marsden, C. J.; Regitz, M.; Bertrand, G. Chem.-Eur. J. 1999, 5, 274-279
17. Alcaraz, G.; Wecker, U.; Baceiredo, A.; Dahan, F.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1246-1248
18. 1-CBDs have been proposed only as intermediates. See: Hofmann, M. A.; Heydt, H.; Regitz, M. Synthesis 2001, 463-467
19. Binger, P.; Milczarek, R.; Mynott, R.; Regitz, M. J. Organomet. Chem. 1987, 323, C35-C38
20. Binger, P.; Haas, J.; Herrman, A. T.; Langhauser, F.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1991, 30, 310-312
21. Hibbs, D. E.; Hursthouse, M. B.; Jones, C.; Richards, A. F.; Francis, M. D.; Dickson, R. S.; Junk, P. C. Organometallics 1999, 18, 4838-4844
22. Schoeller, W. W.; Busch, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 617-619
23. Slootweg, J. C.; Lammertsma, K. Sci. Synth. 2009, 42, 15-36
24. Lammertsma, K. Top. Curr. Chem. 2003, 229, 95-119
25. 1-CBDs. See: Regitz, M. J. Heterocycl. Chem. 1994, 31, 663-677
26. Heydt, H.; Ehle, M.; Haber, S.; Hoffmann, J.; Wagner, O.; Göller, A.; Clark, T.; Regitz, M. Chem. Ber. 1997, 130, 711-723
27. Mathey, F.; Tran Huy, N. H.; Marinetti, A. Helv. Chim. Acta 2001, 84, 2938-2957
28. Lammertsma, K.; Vlaar, M. J. M. Eur. J. Org. Chem. 2002, 1127-1138
29. Borst, M. L. G.; Bulo, R. E.; Gibney, D. J.; Alem, Y.; de Kanter, F. J. J.; Ehlers, A. W.; Schakel, M.; Lutz, M.; Spek, A. L.; Lammertsma, K. J. Am. Chem. Soc. 2005, 127, 16985-16999
30. Jansen, H.; Samuels, M. C.; Couzijn, E. P. A.; Slootweg, J. C.; Ehlers, A. W.; Chen, P.; Lammertsma, K. Chem.-Eur. J. 2010, 16, 1454-1458
31. Zurmühlen, F.; Regitz, M. J. Organomet. Chem. 1987, 332, C1-C5
32. CCDC 796777 (5a) and 796778 (5b) 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. For the experimental details of the X-ray crystal structure determinations, see the Supporting Information.
33. Binger, P.; Biedenbach, B.; Schneider, R.; Regitz, M. Synthesis 1989, 960-961
34. Himmel, D.; Seitz, M.; Scheer, M. Z. Anorg. Allg. Chem. 2004, 630, 1220-1228
35. Wolf, R.; Slootweg, J. C.; Ehlers, A. W.; Hartl, F.; de Bruin, B.; Lutz, M.; Spek, A. L.; Lammertsma, K. Angew. Chem., Int. Ed. 2009, 48, 3104-3107
36. Frisch, M. J.; Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
37. The ETS-NOCV analysis (see: Mitoraj, M. P.; Michalak, A.; Ziegler, T. J. Chem. Theory Comput. 2009, 5, 962-975) was performed at the BP86/TZP level using ADF2009.01; see the Supporting Information for details.
38. ax conversion. exo-6a′ is a saddle point on the PES for the rearrangement of 4a′ into exo-7a′.
39. Scheschkewitz, D.; Amii, H.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Angew. Chem., Int. Ed. 2004, 43, 585-587
40. Gandon, V.; Bourg, J.-B.; Tham, F. S.; Schoeller, W. W.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 155-159
41. Breher, F. Coord. Chem. Rev. 2007, 251, 1007-1043
42. Couzijn, E. P. A.; Slootweg, J. C.; Ehlers, A. W.; Lammertsma, K. J. Am. Chem. Soc. 2010, 132, 18127-18140
43. 2〉 = 1.056).
44. It is likely that phosphacyclobutadiene 9a′ is destabilized by its antiaromatic character. For aromatic dianionic cyclobutadienes, see: Sebastian, M.; Nieger, M.; Szieberth, D.; Nyulászi, L.; Niecke, E. Angew. Chem., Int. Ed. 2004, 43, 637-641 and references therein
45. Sekiguchi, A.; Matsuo, T.; Watanabe, H. J. Am. Chem. Soc. 2000, 122, 5652-5653
46. Goumans, T. P. M.; Ehlers, A. W.; van Hemert, M. C.; Rosa, A.; Baerends, E. J.; Lammertsma, K. J. Am. Chem. Soc. 2003, 125, 3558-3567