Reactive N-protonated isocyanate species stabilized by bis(μ-hydroxo) divanadium(IV)-substituted polyoxometalate

Angewandte Chemie - International Edition

Volumn 51, Issue 31, 2012, Pages 7715-7718

  Uehara, Kazuhiro ^a   Fukaya, Keisuke ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

cyclotrimerization; intermediates; isocyanates; polyoxometalates; protonation

Indexed keywords

CYCLOTRIMERIZATION; INTERMEDIATES; ISOCYANATES; KEGGIN-TYPE; PHENYL ISOCYANATES; POLYOXOMETALATES;

AMMONIUM COMPOUNDS; OXIDES; X RAY CRYSTALLOGRAPHY;

PROTONATION;

ISOCYANIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; POLYOXOMETALATE I; PROTON; TUNGSTEN DERIVATIVE; VANADIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; TEMPERATURE;

ISOCYANATES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PROTONS; TEMPERATURE; TUNGSTEN COMPOUNDS; VANADIUM;

EID: 84864401999     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108205     Document Type: Article

References (81)

1. Thematic issues on polyoxometalate: Chem. Rev. (Ed.: C. L. Hill) 1998, 98, 1
2. Polyoxometalate Chemistry for Nano-Composite Design (Eds.:, T. Yamase, M. T. Pope,), Kluwer, Dordrecht, The Netherlands, 2002
3. Catalysts for Fine Chemical and Synthesis. Catalysis by Polyoxometalates 2 (Ed.:, I. V. Kozhevnikov,), Wiley, Chichester, UK, 2002
4. M. T. Pope, Comprehensive Coordination Chemistry II, Vol. 4 (Eds.:, A. G. Wedd, J. A. McCleverty, T. J. Meyer,), Elsevier, New York, 2004, pp. 635
5. C. L. Hill, Comprehensive Coordination Chemistry II, Vol. 4 (Eds.:, A. G. Wedd, J. A. McCleverty, T. J. Meyer,), Elsevier, New York, 2004, p. 679
6. R. Neumann, Modern Oxidation Methods (Ed.:, J. E. Bäckvall,), Wiley-VCH, Weinheim, 2004, p. 223
7. B. S. Bassil, U. Kortz, Dalton Trans. 2011, 40, 9649-9661
8. T. Okuhara, N. Mizuno, M. Misono, Adv. Catal. 1996, 41, 113-252
9. Zeolite, Clay, and Heteropoly Acid in Organic Reactions (Eds.:, Y. Izumi, K. Urabe, A. Onaka,), Kodansha, Tokyo, 1992.
10. J. Macht, M. J. Janik, M. Neurock, E. Iglesia, J. Am. Chem. Soc. 2008, 130, 10369-10379
11. J. Macht, M. J. Janik, M. Neurock, E. Iglesia, Angew. Chem. 2007, 119, 8010-8014
12. Angew. Chem. Int. Ed. 2007, 46, 7864-7868.
13. W. H. Knoth, R. L. Harlow, J. Am. Chem. Soc. 1981, 103, 4265-4266.
14. Carbocation Chemistry (Eds.:, G. A. Olah, G. K. S. Prakash,), Wiley Interscience, New York, 2004
15. G. A. Olah, J. Org. Chem. 2001, 66, 5944-5957
16. T. Laube, Chem. Rev. 1998, 98, 1277-1312
17. T. Laube, Acc. Chem. Res. 1995, 28, 399-405
18. H. Grützmacher, C. M. Marchand, Coord. Chem. Rev. 1997, 163, 287-344
19. C. A. Reed, Acc. Chem. Res. 2010, 43, 121-128.
20. M. Bochmann, Acc. Chem. Res. 2010, 43, 1267-1278
21. P. G. Cozzi, F. Benfatti, Angew. Chem. 2010, 122, 264-267
22. Angew. Chem. Int. Ed. 2010, 49, 256-259
23. T. Laube, Angew. Chem. 1996, 108, 2939-2940
24. Angew. Chem. Int. Ed. Engl. 1996, 35, 2765-2766.
25. H. Alvaro Galué, J. Oomens, Angew. Chem. 2011, 123, 7142-7145
26. Angew. Chem. Int. Ed. 2011, 50, 7004-7007
27. E. Stavitski, E. A. Pidko, M. H. F. Kox, E. J. M. Hensen, R. A. van Santen, B. M. Weckhuysen, Chem. Eur. J. 2010, 16, 9340-9348
28. M. H. F. Kox, E. Stavitski, J. C. Groen, J. Pérez-Rmírez, F. Kapteijn, B. M. Weckhuysen, Chem. Eur. J. 2008, 14, 1718-1725
29. M. J. Truitt, S. S. Toporek, R. Rovira-Truitt, J. L. White, J. Am. Chem. Soc. 2006, 128, 1847-1852
30. M. Winkler, W. Sander, Angew. Chem. 2000, 112, 2091-2094
31. Angew. Chem. Int. Ed. 2000, 39, 2014-2016
32. R. D. Bolskar, R. S. Mathur, C. A. Reed, J. Am. Chem. Soc. 1996, 118, 13093-13094.
33. C. Douvris, E. S. Stoyanov, F. S. Tham, C. A. Reed, Chem. Commun. 2007, 1145-1147
34. M. G. Davlieva, S. V. Lindeman, I. S. Neretin, J. K. Kochi, J. Org. Chem. 2005, 70, 4013-4021
35. S. V. Lindeman, I. S. Neretin, M. G. Davlieva, J. K. Kochi, J. Org. Chem. 2005, 70, 3263-3266
36. T. Kato, C. A. Reed, Angew. Chem. 2004, 116, 2968-2971
37. Angew. Chem. Int. Ed. 2004, 43, 2908-2911
38. H. Kawai, T. Nagasu, T. Takeda, K. Fujiwara, T. Tsuji, M. Ohkita, J. Nishida, T. Suzuki, Tetrahedron Lett. 2004, 45, 4553-4558
39. C. A. Reed, K.-C. Kim, E. S. Stoyanov, D. Stasko, F. S. Tham, L. J. Mueller, P. D. W. Boyd, J. Am. Chem. Soc. 2003, 125, 1796-1804
40. M. Schormann, S. Garratt, D. L. Hughes, J. C. Green, M. Bochmann, J. Am. Chem. Soc. 2002, 124, 11266-11267
41. S. Hollenstein, T. Laube, J. Am. Chem. Soc. 1993, 115, 7240-7245
42. E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, J. Chem. Soc. Chem. Commun. 1991, 841-842.
43. S. Ozaki, Chem. Rev. 1972, 72, 457-496
44. G. A. Olah, J. Nishimura, P. Kreienbühl, J. Am. Chem. Soc. 1973, 95, 7672-7680
45. E. A. Castro, R. D. Moodie, P. J. Sansom, J. Chem. Soc. Perkin Trans. 2 1985, 737-741
46. K. R. Birdwhistell, T. Boucher, M. Ensminger, S. Harris, M. Johnson, S. Toporek, Organometallics 1993, 12, 1023-1025
47. J. Louie, Curr. Org. Chem. 2005, 9, 605-623
48. A. Antiñolo, S. García-Yuste, A. Otero, E. Villaseñor, J. Organomet. Chem. 2007, 692, 4436-4447
49. W. Darwish, E. Seilel, R. Käsmarker, K. Harms, J. Sundermeyer, Dalton Trans. 2011, 40, 1787-1794
50. S. R. Dubberley, A. Friedrich, D. A. Willman, P. Mountford, U. Radius, Chem. Eur. J. 2003, 9, 3634-3654
51. E. B. Brouwer, P. Legzdins, S. J. Rettig, K. J. Ross, Organometallics 1993, 12, 4234-4240
52. Z. Karpas, W. J. Stevens, T. J. Buckley, R. Metz, J. Phys. Chem. 1985, 89, 5274-5278
53. + has been isolated:, A. Schulz, A. Vilinger, Chem. Eur. J. 2010, 16, 7276-7281.
54. N. E. Brese, M. O'Keeffe, Acta Crystallogr. Sect. B 1991, 47, 192-197.
55. K. Uehara, N. Mizuno, J. Am. Chem. Soc. 2011, 133, 1622-1625.
56. A. Ozarowski, D. Reinen, Inorg. Chem. 1986, 25, 1704-1708
57. P. L. W. Tregenna-Piggott, H.-P. Andres, G. J. McIntyre, S. P. Best, C. C. Wilson, J. A. Cowan, Inorg. Chem. 2003, 42, 1350-1365
58. H. Henke, Z. Kristallogr. 2003, 218, 617-625.
59. Spectroscopic Identification of Organic Compounds (Eds.:, R. M. Silverstein, G. C. Bassler, T. C. Morrill,), Wiley, New York, 1991
60. Infrared and Raman Spectra of Inorganic and Coordination Compounds (Ed:, K. Nakamoto,), Wiley, New York, 1978.
61. G. K. Surya, G. Rasul, G. A. Olah, J. Phys. Chem. 1996, 100, 15805-15809
62. M. G. Davlieva, S. V. Lindeman, I. S. Neretin, J. K. Kochi, New J. Chem. 2004, 28, 1568-1574
63. G. A. Olah, A. M. White, J. Am. Chem. Soc. 1967, 89, 7072-7075.
64. Molecular visualization program: U. Varetto, Molekel 5.4, Swiss National Supercomputing Centre (CSCS), Lugano (Switzerland).
65. M. J. Frisch, et al., Gaussian 09, Revision B.01 (Gaussian, Inc., Wallingford CT, 2009).
66. E. V. Feshina, V. P. Feshin, Russ. J. Gen. Chem. 2006, 76, 970-973
67. V. P. Feshin, E. V. Feshina, Russ. J. Gen. Chem. 2006, 76, 966-969.
68. M. Roman, B. Andrioletti, M. Lemaire, J.-M. Bernard, J. Schwartz, P. Barbeau, Tetrahedron 2011, 67, 1506-1510
69. F. Paul, S. Moulin, O. Piechaczyk, P. L. Floch, J. A. Osborn, J. Am. Chem. Soc. 2007, 129, 7294-7304
70. Z. Pusztai, G. Vlád, A. Bodor, I. T. Horváth, H. J. Laas, R. Halpaap, F. U. Richter, Angew. Chem. 2006, 118, 113-116
71. Angew. Chem. Int. Ed. 2006, 45, 107-111
72. Y. Li, H. Matsumura, M. Yamanaka, T. Takahashi, Tetrahedron 2004, 60, 1393-1400
73. H. A. Duong, M. J. Cross, J. Louie, Org. Lett. 2004, 6, 4679-4681
74. S. R. Foley, G. P. A. Yap, D. S. Richeson, Organometallics 1999, 18, 4700-4705
75. J.-S. Tang, J. G. Verkade, Angew. Chem. 1993, 105, 934-936
76. Angew. Chem. Int. Ed. Engl. 1993, 32, 896-898
77. Y. Nambu, T. Endo, J. Org. Chem. 1993, 58, 1932-1934
78. R. J. P. Corriu, G. F. Lanneau, V. D. Mehta, Heteroat. Chem. 1991, 2, 461-463
79. Y. Taguchi, I. Shibuya, M. Yasumoto, T. Tsuchiya, K. Yonemoto, Bull. Chem. Soc. Jpn. 1990, 63, 3486-3489.
80. F. U. Richter, Chem. Eur. J. 2009, 15, 5200-5202
81. R. Richter, H. Ulrich, J. Org. Chem. 1981, 46, 3011-3015.