Triple-bond reactivity of an AsP complex intermediate: Synthesis stemming from molecular arsenic, As4

Journal of the American Chemical Society

Volumn 131, Issue 44, 2009, Pages 16233-16243

  Spinney, Heather A ^a   Piro, Nicholas A ^a   Cummins, Christopher C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION COMPLEX; DIELS ALDER ADDUCTS; FUNCTIONALIZATIONS; GROUP 15 ELEMENT; ORGANIC MEDIA; PENTACARBONYL; PURE SUBSTANCES; REACTIVE INTERMEDIATE; THERMAL GENERATION; TRAPPING REACTION; X-RAY DIFFRACTION METHOD;

ARSENIC; ARSENIC COMPOUNDS; FLUORINE CONTAINING POLYMERS; LIGHT; MOLYBDENUM; NIOBIUM; NIOBIUM COMPOUNDS; OLEFINS; PHOSPHORUS; TUNGSTEN; X RAY DIFFRACTION ANALYSIS;

MOLYBDENUM COMPOUNDS;

ARSENIC; NIOBIUM; TUNGSTEN;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; NONHUMAN; X RAY DIFFRACTION;

EID: 70450171011     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906550h     Document Type: Article

References (81)

1. Rodionov, A.; Kalendarev, R.; Eiduss, J.; Zhukovskii, Y. J. Mol. Struct. 1996, 380, 257-266.
2. Bettendorff, A. Annalen Chem. Pharm. 1867, 144, 110-114.
3. Linck, G. E. Chem. Ber. 1899, 32, 881-897.
4. Stock, A.; Siebert, W. Chem. Ber. 1905, 38, 966-968.
5. Erdmann, H.; von Unruh, M. Z. Anorg. Chem. 1902, 32, 437-452.
6. Scherer, O. J.; Sitzmann, H.; Wolmershäuser, G. J. Organomet. Chem. 1986, 309, 77-86.
7. (a) Scherer, O. J.; Sitzmann, H.; Wolmershäuser, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 212-213.
8. (b) Scherer, O. J.; Wiedemann, W.; Wolmershäuser, G. J. Organomet. Chem. 1989, 361, C11-C14.
9. (c) Scherer, O. J.; Vondung, J.; Wolmershäuser, G. J. Organomet. Chem. 1989, 376, C35-C38.
10. (d) Scherer, O. J.; Blath, C.; Wolmershäuser, G. J. Organomet. Chem. 1990, 387, C21-C24.
11. (e) Scherer, O. J.; Wiedemann, W.; Wolmershäuser, G. Chem. Ber. 1990, 123, 3-6.
12. (f) Scherer, O. J.; Winter, R.; Heckmann, G.; Wolmershäuser, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 850-852.
13. (g) Scherer, O. J.; Blath, C.; Heckmann, G.; Wolmershäuser, G. J. Organomet. Chem. 1991, 409, C15-C18.
14. (h) Scherer, O. J. Acc. Chem. Res. 1999, 32, 751-762.
15. (a) Scherer, O. J.; Braun, J.; Wolmershäuser, G. Chem. Ber. 1990, 123, 471-475.
16. (b) Scherer, O. J.; Braun, J.; Walther, P.; Wolmersha ̈user, G. Chem. Ber. 1992, 125, 2661-2665.
17. (c) Scherer, O. J.; Kemény, G.; Wolmershäuser, G. Chem. Ber. 1995, 128, 1145-1148.
18. (a) Di Vaira, M.; Ghilardi, C. A.; Midollini, S.; Sacconi, L. J. Am. Chem. Soc. 1978, 100, 2550-2551.
19. (b) Di Vaira, M.; Midollini, S.; Sacconi, L.; Zanobini, F. Angew. Chem., Int. Ed. Engl. 1978, 17, 676-677.
20. (a) Tan, R. P.; Comerlato, N. M.; Powell, D. R.; West, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 1217-1218.
21. (b) Fanta, A. D.; Tan, R. P.; Comerlato, N. M.; Driess, M.; Powell, D. R.; West, R. Inorg. Chim. Acta 1992, 198-200, 733-739.
22. Figueroa, J. S.; Cummins, C. C. J. Am. Chem. Soc. 2003, 125, 4020-4021.
23. Figueroa, J. S.; Cummins, C. C. Angew. Chem., Int. Ed. 2004, 43, 984-988.
24. (a) Figueroa, J. S.; Cummins, C. C. J. Am. Chem. Soc. 2004, 126, 13916-13917.
25. (b) Figueroa, J. S.; Cummins, C. C. Angew. Chem., Int. Ed. 2005, 44, 4592-4596.
26. (c) Figueroa, J. S.; Cummins, C. C. Dalton Trans. 2006, 2161-2168.
27. Niecke, E.; Nieger, M.; Reichert, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 1715-1716.
28. Piro, N. A.; Figueroa, J. S.; McKellar, J. T.; Cummins, C. C. Science 2006, 313, 1276-1279.
29. Piro, N. A.; Cummins, C. C. J. Am. Chem. Soc. 2008, 130, 9524-9535.
30. Piro, N. A.; Cummins, C. C. Inorg. Chem. 2007, 46, 7387-7393.
31. Cossairt, B. M.; Diawara, M.-C.; Cummins, C. C. Science 2009, 323, 602.
32. Ugai, Y. A.; Semenova, G. V.; Berendt, E.; Goncharov, E. G. Russ. J. Phys. Chem. 1979, 53, 576-577.
33. Karakaya, I.; Thompson, W. T. J. Phase Equilib. 1991, 12, 343-346
34. Yee, K. K.; Jones, W. E. Chem. Commun. 1969, 586a.
35. Leung, F.; Cooke, S. A.; Gerry, M. C. L. J. Mol. Spectrosc. 2006, 238, 36-41.
36. Gingerich, K. A.; Cocke, D. L.; Kordis, J. J. Phys. Chem. 1974, 78, 603-606.
37. (a) Davies, J. E.; Kerr, L. C.; Mays, M. J.; Raithby, P. R.; Tompkin, P. K.; Woods, A. D. Angew. Chem., Int. Ed. 1998, 37, 1428-1429.
38. (b) Davies, J. E.; Mays, M. J.; Raithby, P. R.; Shields, G. P.; Tompkin, P. K.; Woods, A. D. J. Chem. Soc., Dalton Trans. 2000, 1925-1930.
39. Herrmann, W. A.; Koumbouris, B.; Zahn, T.; Ziegler, M. L. Angew. Chem., Int. Ed. Engl. 1984, 23, 812-814.
40. Fenske, D.; Fleischer, H.; Persau, C. Angew. Chem., Int. Ed. Engl. 1989, 28, 1665-1667.
41. DiMaio, A.-J.; Baldacchini, C. J.; Rheingold, A. L. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1990, 46, 492-494.
42. Pyykkö, P.; Atsumi, M. Chem.-Eur. J. 2009, 15, 186-197.
43. Pyykkö, P.; Atsumi, M. Chem.-Eur. J., accepted.
44. Chen, H.; Olmstead, M. M.; Pestana, D. C.; Power, P. P. Inorg. Chem. 1991, 30, 1783-1787.
45. Bouslikhane, M.; Gornitzka, H.; Escudie, J.; Ranaivonjatovo, H. J. Organomet. Chem. 2001, 619, 275-279.
46. Hirsch, A.; Chen, Z.; Jiao, H. Angew. Chem., Int. Ed. 2001, 40, 2834-2838.
47. Maxwell, L. R.; Hendricks, S. B.; Mosley, V. M. J. Chem. Phys. 1935, 3, 699-709.
48. Please see the Supporting Information.
49. Scheer, M.; Müller, J.; Häser, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2492-2496.
50. Mösch-Zanetti, N. C.; Schrock, R. R.; Davis, W. M.; Wanninger, K.; Seidel, S. W.; O'Donoghue, M. B. J. Am. Chem. Soc. 1997, 119, 11037-11048.
51. (a) Gascoin, F.; Sevov, S. C. Angew. Chem., Int. Ed. 2002, 41, 1232-1234.
52. (b) Gascoin, F.; Sevov, S. C. Inorg. Chem. 2003, 42, 904-907.
53. (c) Gascoin, F.; Sevov, S. C. Inorg. Chem. 2003, 42, 8567-8571.
54. Pyykkö, P.; Riedel, S.; Patzschke, M. Chem.-Eur. J. 2005, 11, 3511-3520.
55. Cowley, A. H.; Lasch, J. G.; Norman, N. C.; Pakulski, M.; Whittlesey, B. R. J. Chem. Soc., Chem. Commun. 1983, 881-882.
56. Schinkels, B.; Ruban, A.; Nieger, M.; Niecke, E. Chem. Commun. 1997, 293-294.
57. Brask, J. K.; Fickes, M. G.; Sangtrirutnugul, P.; Durà- Vilà, V.; Odom, A. L.; Cummins, C. C. Chem. Commun. 2001, 1676-1677.
58. Agarwal, P.; Piro, N.; Meyer, K.; Müller, P.; Cummins, C. Angew. Chem., Int. Ed. 2007, 46, 3111-3114.
59. As commented by a reviewer, the trapping of the AsP fragment with the dienes is somewhat tenuous, since it is based solely on the NMR shift obtained in a mixture of compounds.
60. Cherry, J.-P.; Stephens, F. H.; Johnson, M. J. A.; Diaconescu, P. L.; Cummins, C. C. Inorg. Chem. 2001, 40, 6860-6862.
61. Stephens, F. H.; Johnson, M. J. A.; Cummins, C. C.; Kryatova, O. P.; Kryatov, S. V.; Rybak-Akimova, E. V.; McDonough, J. E.; Hoff, C. D. J. Am. Chem. Soc. 2005, 127, 15191-15200.
62. Umbarkar, S.; Sekar, P.; Scheer, M. J. Chem. Soc., Dalton Trans. 2000, 1135-1137.
63. Esterhuysen, C.; Frenking, G. Chem.-Eur. J. 2003, 9, 3518-3529.
64. http://microcal.com, Microcal(TM) Origin Version 6.0, Copyright 1991-1999, Microcal Software, Inc.
65. 5 present in solution had already converted to the niobium imido 5.
66. Sheldrick, G. M. SADABS; Bruker AXS Inc.: 2005.
67. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, 467-473.
68. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112-122.
69. Sheldrick, G. M. SHELXL-97; University of Göttingen: 1997.
70. Müller, P.; Herbst-Irmer, R.; Spek, A. L.; Schneider, T. R.; Sawaya, M. R. Crystal structure refinement: A crystallographer's guide to SHELXL; Oxford University Press: Oxford, 2006.
71. This material is available free of charge at http://www.ccdc.cam.ac.uk/ data- request/cif.
72. (a) te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. J. Comput. Chem. 2001, 22, 931-967.
73. (b) http://www.scm.com, ADF 2006.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands.
74. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
75. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
76. (b) Handry, N. C.; Co-hen, A. J. Mol. Phys. 2001, 99, 403-412.
77. (c) Baker, J.; Pulay, P. J. Comput. Chem. 2003, 24, 1184-1191.
78. (a) van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1993, 99, 4597-4610.
79. (b) van Lenthe, E.; Baerends, E. J.; Snijders, J. G. J. Chem. Phys. 1994, 101, 9783-9792.
80. (c) van Lenthe, E.; Ehlers, A.; Baerends, E.-J. J. Chem. Phys. 1999, 110, 8943-8953.
81. Michalak, A.; DeKock, R. L.; Ziegler, T. J. Phys. Chem. A 2008, 112, 7256-7263.