Nonmetal-mediated fragmentation of P4: Isolation of P 1 and P2 bis(carbene) adducts

Angewandte Chemie - International Edition

Volumn 48, Issue 30, 2009, Pages 5530-5533

  Back, Olivier ^a   Kuchenbeiser, Glenn ^a   Donnadieu, Bruno ^a   Bertrand, Guy ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Carbenes; Cyclopropenylidenes; Fragmentation; P P activation; Phosphorus

Indexed keywords

CARBENES; CYCLOPROPENYLIDENES; ENVIRONMENTALLY-FRIENDLY; FRAGMENTATION; P-P ACTIVATION; ROOM TEMPERATURE; WHITE PHOSPHORUS;

TRANSITION METALS;

PHOSPHORUS;

EID: 70349929027     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902344     Document Type: Article

References (86)

1. For recent examples of small molecule activation by nonmet al.s other than carbenes, see: a) S. J. Geier, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 3476-3477;
2. M. Ullrich, A. J. Lough, D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 52-53;
3. S. N. Riduan, Y. Zhang, J. Y. Ying, Angew. Chem. 2009, 121, 3372-3375
4. Angew Chem. Int. Ed. 2009, 48, 3322-3325;
5. A. Jana, C. Schulzke, H. W. Roesky, J. Am. Chem. Soc. 2009, 131, 4600-4601;
6. Z. L. Zhu, X. P. Wang, Y. Peng, H. Lei, J. C. Fettinger, E. Rivard, P. P. Power, Angew. Chem. 2009, 121, 2065-2068
7. Angew Chem. Int. Ed. 2009, 48, 2031-2034;
8. Y. Peng, M. Brinda, B. D. Ellis, J. C. Fettinger, E. Rivard, P. P. Power, Chem. Commun. 2009, 6042-6044;
9. Y Peng, B. D. Ellis, X. P. Wang, J. C. Fettinger, P. P. Power, J. Am. Chem. Soc. 2008, 130, 12268-12269;
10. M. A. Dureen, D. W. Stephan, Chem. Commun. 2008, 4303-4305;
11. P. A. Chase, D. W. Stephan, Angew. Chem. 2008, 120, 7543-7547
12. Angew Chem. Int. Ed. 2008, 47, 7433-7437;
13. D. Holschumacher, T. Bannenberg, C. G. Hrib, P. G. Jones, M. Tamm, Angew. Chem. 2008, 120, 7538-7542
14. Angew Chem. Int. Ed. 2008, 47, 7428-7432;
15. P. Spies, S. Schewendemann, S. Lange, G. Kehr, R. Frohlich, G. Erker, Angew. Chem. 2008, 120, 7654-7657
16. Angew Chem. Int. Ed. 2008, 47, 7543-7546;
17. V. Sumerin, F. Schulz, M. Atsumi, C. Wang, M. Nieger, M. Leskela, T. Repo, P. Pyykko, B. Rieger, J. Am. Chem. Soc. 2008, 130, 14117-14119;
18. V. Sumerin, F. Schulz, M. Nieger, M. T. R. Leskela, B. Rieger, Angew. Chem. 2008, 120, 6090-6092
19. Angew Chem. Int. Ed. 2008, 47, 6001-6003;
20. n) G. C. Welch, R. R. S. Juan, J. D. Masuda, D. W. Stephan, Science 2006, 314, 1124-1126.
21. a) Y. Z. Wang, B. Quillian, P. R. Wei, C. S. Wannere, Y. Xie, R. B. King, H. F. Schaefer, P. v. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2007, 129, 12412-12413;
22. Y. Z. Wang, B. Quillian, P. R. Wei, Y. Xie, C. S. Wannere, R. B. King, H. F. Schaefer, P. v. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2008, 130, 3298-3299.
23. Y. Z. Wang, Y. M. Xie, P. R. Wei, R. B. King, H. F. Schaefer, P. von R. Schleyer, Science 2008, 321, 1069-1071
24. See also: C. A. Dyker, G. Bertrand, Science 2008, 321, 1050-1051.
25. a) L. B. Knight, K. Kerr, P. K. Miller, C. A. Arrington, J. Phys. Chem. 1995, 99, 16842-16848;
26. A. H. Cowley, ACS Symp. Ser. 2006, 917, 2-19;
27. R. West, ACS Symp. Ser. 2006, 917, 166-178;
28. P. P. Power, Chem. Rev. 1999, 99, 3463-3503.
29. V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Angew. Chem. 2006, 118, 3568-3571
30. Angew Chem. Int. Ed. 2006, 45, 3488-3491.
31. G. D. Frey, V. Lavallo, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2007, 316, 439-441.
32. 3 activation by a transition met al. have been reported, see: a) C. M. Fafard, D. Adhikari, B. M. Foxman, D. J. Mindiola, O. V. Ozerov, J. Am. Chem. Soc. 2007, 129, 10318-10319;
33. T. E. Hanna, E. Loblovski, P. J. Chirik, Eur. J. Inorg. Chem. 2007, 2677-2685;
34. Y. Nakajima, H. Kameo, H. Suzuki, Angew. Chem. 2006, 118, 964-966
35. Angew Chem. Int. Ed. 2006, 45, 950-952;
36. J. Zhao, A. S. Goldman, J. F. Hartwig, Science 2005, 307, 1080-1082.
37. 3 have recently been reported: V. Lavallo, G. D. Frey, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Angew. Chem. 2008, 120, 5302-5306
38. Angew Chem. Int. Ed. 2008, 47, 5224-5228.
39. a) D. E. C. Corbridge, Phosphorus-An Outline of its Chemistry, Biochemistry and Technology, 5th ed., Elsevier, Amsterdam, 1995;
40. J. Emsley, The 13th Element: The Sordid Tale of Murder, Fire, and Phosphorus, Wiley, New York, 2002.
41. For recent reviews, see: a) J. S. Figueroa, C. C. Cummins, Dalton Trans. 2006, 2161-2168;
42. C. C. Cummins, Angew. Chem. 2006, 118, 876-884
43. Angew Chem. Int. Ed. 2006, 45, 862-870;
44. M. Peruzzini, L. Gonsalvi, A. Romerosa, Chem. Soc. Rev. 2005, 34, 1038-1047;
45. M. Peruzzini, R. R. Abdreimova, Y. Budnikova, A. Romerosa, O. J. Scherer, H. Sitzmann, J. Organomet. Chem. 2004, 689, 4319-4331;
46. M. Ehses, A. Romerosa, M. Peruzzini, Top. Curr. Chem. 2002, 220, 107-140.
47. For recent reports, see: a) P. Barbaro, M. Di Vaira, M. Peruzzini, S. S. Costantini, P. Stoppioni, Inorg. Chem. 2009, 48, 1091-1096;
48. W. W. Seidel, O. T. Summerscales, B. O. Patrick, M. D. Fryzuk, Angew. Chem. 2009, 121, 121-123
49. Angew Chem. Int. Ed. 2009, 48, 115-117;
50. Barbaro, M. Di Vaira, M. Peruzzini, S. S. Costantini, P. Stoppioni, Angew. Chem. 2008, 120, 4497-4499
51. Angew Chem. Int. Ed. 2008, 47, 4425-4427;
52. M. Caporali, P. Barbaro, L. Gonsalvi, A. Ienco, D. Yakhvarov, M. Peruzzini, Angew. Chem. 2008, 120, 3826-3828
53. Angew Chem. Int. Ed. 2008, 47, 3766-3768.
54. 4 has also been reported; for recent examples, see: a) J. J. Weigand, M. Holthausen, R. Frolich, Angew. Chem. 2009, 121, 301-304
55. Angew Chem. Int. Ed. 2009, 48, 295-298;
56. W. T. K. Chan, F. Garcia, A. D. Hopkins, L. C. Martin, M. McPartlin, D. S. Wright, Angew. Chem. 2007, 119, 3144-3146
57. Angew Chem. Int. Ed. 2007, 46, 3084-3086;
58. Y. Xiong, S. Yao, M. Brym, M. Driess, Angew. Chem. 2007, 119, 4595-4597
59. Angew Chem. Int. Ed. 2007, 46, 4511-4513;
60. A. R. Fox, R. J. Wright, E. Rivard, P. P. Power, Angew. Chem. 2005, 117, 7907-7911
61. Angew Chem. Int. Ed. 2005, 44, 7729-7733;
62. H. W. Lerner, M. Bolte, K. Karaghiosoff, M. Wagner, Organomet al.lics 2004, 23, 6073-6076.
63. a) J. D. Masuda, W W Schoeller, B. Donnadieu, G. Bertrand, Angew. Chem. 2007, 119, 7182-7185
64. Angew Chem. Int. Ed. 2007, 46, 7052-7055;
65. J. D. Masuda, W. W. Schoeller, B. Donnadieu, G. Bertrand, J. Am. Chem. Soc. 2007, 129, 14180-14181
66. See also: J. M. Lynam, Angew. Chem. 2008, 120, 843-845
67. Angew Chem. Int. Ed. 2008, 47, 831-833.
68. a) B. M. Cossairt, M. C. Diawara, C. C. Cummins, Science 2009, 323, 602-602;
69. B. M. Cossairt, C C Cummins, Angew. Chem. 2008, 120, 8995-8998
70. Angew Chem. Int. Ed. 2008, 47, 8863-8866;
71. N. A. Piro, C. C. Cummins, J. Am. Chem. Soc. 2008, 130, 9524-9535;
72. A. R. Fox, C. R. Clough, N. A. Piro, C. C. Cummins, Angew. Chem. 2007, 119, 991-994
73. Angew Chem. Int. Ed. 2007, 46, 973-976;
74. N. A. Piro, J. S. Figueroa, J. T. McKellar, C C Cummins, Science 2006, 313, 1276-1279.
75. V. Lavallo, J. Mafhouz, Y Canac, B. Donnadieu, W W Schoeller, G Bertrand, J. Am. Chem. Soc. 2004, 126, 8670-8671.
76. CCDC 730165 (D), 730166 (E), 730167 (F), and 730168 (G) 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.
77. a) V. Lavallo, Y Canac, C Prasang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851-5855
78. Angew Chem. Int. Ed. 2005, 44, 5705-5709;
79. R. Jazzar, R. D. Dewhurst, J. B. Bourg, B. Donnadieu, Y Canac, G. Bertrand, Angew. Chem. 2007, 119, 2957-2960
80. Angew Chem. Int. Ed. 2007, 46, 2899-2902.
81. V. D. Romanenko, L. S. Kachkovskaya, L. N. Markovskii, Zh. Obshch. Khim. 1985, 55, 2140-2141.
82. Y. Z. Wang, Y. M. Xie, P. R. Wei, R. B. King, H. F. Schaefer, P. von R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2008, 130, 14970-14971.
83. V. Lavallo, Y. Canac, B. Donnadieu, W. W. Schoeller, G. Bertrand, Science 2006, 312, 722-724.
84. A. Schmidpeter, S. Lochschmidt, A. Willhalm, Angew. Chem. 1983, 95, 561-562
85. Angew Chem. Int. Ed. Engl. 1983, 22, 545-546.
86. B. D. Ellis, C. A. Dyker, A. Decken, C. L. B. Macdonald, Chem. Commun. 2005, 1965-1967.