Formation of silicon centered spirocyclic compounds: Reaction of N-heterocyclic stable silylene with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine

Inorganic Chemistry

Volumn 50, Issue 7, 2011, Pages 3028-3036

  Azhakar, Ramachandran ^a   Sarish, Sankaranarayana Pillai ^a   Tavčar, Gašper ^a   Roesky, Herbert W ^a   Hey, Jakob ^a   Stalke, Dietmar ^a   Koley, Debasis ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIPHENYLHYDRAZINE; AZO COMPOUND; CARBAMIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND; ORGANOSILICON DERIVATIVE; PHENYLHYDRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZO COMPOUNDS; CARBAMATES; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; PHENYLHYDRAZINES; PYRIDINES; SILANES; SPIRO COMPOUNDS;

EID: 79953217451     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic102566c     Document Type: Article

References (102)

1. Gasper, P. P. and West, R. In The Chemistry of Organic Silicon Compounds, 2 nd ed.; Rappoport, Z. and Apeloig, Y., Eds.; John Wiley and Sons: NewYork, 1999; Vol. 2, Part 3, pp 2463 - 2568
2. Haaf, M.; Schmedake, T. A.; West, R. Acc. Chem. Res. 2000, 33, 704-714
3. Gehrhus, B.; Lappert, M. F. J. Organomet. Chem. 2001, 617-618, 209-223
4. Nagendran, S.; Roesky, H. W. Organometallics 2008, 27, 457-492
5. Arduengo, A. J., III; Bock, H.; Chen, H.; Denk, M.; Dixon, D. A.; Green, J. C.; Herrmann, W. A.; Jones, N. L.; Wagner, M.; West, R. J. Am. Chem. Soc. 1994, 116, 6641-6649
6. Denk, M.; Lennon, R.; Hayashi, R.; West, R.; Belyakov, A. V.; Verne, H. P.; Haaland, A.; Wagner, M.; Metzler, N. J. Am. Chem. Soc. 1994, 116, 2691-2692
7. So, C.-W.; Roesky, H. W.; Magull, J.; Oswald, R. B. Angew. Chem. 2006, 118, 4052-4054
8. Angew. Chem., Int. Ed. 2006, 45, 3948-3950.
9. Sen, S. S.; Roesky, H. W.; Stern, D.; Henn, J.; Stalke, D. J. Am. Chem. Soc. 2010, 132, 1123-1126
10. Driess, M.; Yao, S.; Brym, M.; van Wüllen, C.; Lentz, D. J. Am. Chem. Soc. 2006, 128, 9628-9629
11. Kong, L.; Zhang, J.; Song, H.; Cui, C. Dalton Trans. 2009, 39, 5444-5446
12. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Henn, J.; Stalke, D. Angew. Chem. 2009, 121, 5793-5796
13. Angew. Chem., Int. Ed. 2009, 48, 5683-5686.
14. Nolan, S. P. In N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
15. Glorius, F. In N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer-Verlag: Berlin, 2007.
16. Clavier, H.; Nolan, S. P. Annu. Rep. Prog. Chem., Sect B: Org. Chem. 2007, 103, 193-222
17. Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22
18. Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181-222
19. Harrold, N. D.; Waterman, R.; Hillhouse, G. L.; Cundari, T. R. J. Am. Chem. Soc. 2009, 131, 12872-12873
20. Fustier, M.; Goff, F. L.; Floch, P. L.; Mězailles, N. J. Am. Chem. Soc. 2010, 132, 13108-13110
21. Zimmerman, P. M.; Paul, A.; Musgrave, C. B. Inorg. Chem. 2009, 48, 5418-5433
22. Groysman, S.; Holm, R. H. Inorg. Chem. 2009, 48, 621-627
23. Phillips, E. M.; Riedrich, M.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 13179-13181
24. Mathew, J.; Suresh, C. H. Inorg. Chem. 2010, 49, 4665-4669
25. Catalano, V. J.; Moore, A. L.; Shearer, J.; Kim, J. Inorg. Chem. 2009, 48, 11362-11375
26. Yang, C.-H.; Beltran, J.; Lemaur, V.; Cornil, J.; Hartmann, D.; Sarfert, W.; Fröhlich, R.; Bizzari, C.; Cola, L. D. Inorg. Chem. 2010, 49, 9891-9901
27. Mills, D. P.; Soutar, L.; Lewis, W.; Blake, A. J.; Liddle, S. T. J. Am. Chem. Soc. 2010, 132, 14379-14381
28. Park, H.-J.; Kim, K. H.; Choi, S. Y.; Kim, H.-M.; Lee, W. I.; Kang, Y. K.; Chung, Y. K. Inorg. Chem. 2010, 49, 7340-7352
29. Crees, R. S.; Cole, M. L.; Hanton, L. R.; Sumby, C. J. Inorg. Chem. 2010, 49, 1712-1719
30. Lee, Y.; Li, B.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 11625-11633
31. Sinha, A.; Rahaman, S. M. W.; Sarkar, M.; Saha, B.; Daw, P.; Bera, J. K. Inorg. Chem. 2009, 48, 11114-11122
32. Dash, C.; Shaikh, M. M.; Butcher, R. J.; Ghosh, P. Inorg. Chem. 2010, 49, 4972-4983
33. Fu, C.-F.; Lee, C.-C.; Liu, Y.-H.; Peng, S.-M.; Warsink, S.; Elsevier, C. J.; Chen, J.-T.; Liu, S.-T. Inorg. Chem. 2010, 49, 3011-3018
34. Hsieh, C.-H.; Darensbourg, M. Y. J. Am. Chem. Soc. 2010, 132, 14118-14125
35. Huang, F.; Lu, G.; Zhao, L.; Wang, Z.-X. J. Am. Chem. Soc. 2010, 132, 12388-12396
36. Zhang, W.-Q.; Whitwood, A. C.; Fairlamb, I. J. S.; Lynam, J. M. Inorg. Chem. 2010, 49, 8941-8952
37. Naeem, S.; Delaude, L.; White, A. J. P.; Wilton-Ely, J. D. E. T. Inorg. Chem. 2010, 49, 1784-1793
38. Cade, I. A.; Hill, A. F.; Kämpfe, A.; Wagler, J. Organometallics 2010, 29, 4012-4017
39. Li, R.-E.; Sheu, J.-H.; Su, M.-D. Inorg. Chem. 2007, 46, 9245-9253
40. Bharatam, P. V.; Moudgil, R.; Kaur, D. Inorg. Chem. 2003, 42, 4743-4749
41. Bharatam, P. V.; Moudgil, R.; Kaur, D. Organometallics 2002, 21, 3683-3690
42. Yao, S.; van Wüllen, C.; Sun, X.-Y.; Driess, M. Angew. Chem. 2008, 120, 3294-3297
43. Angew. Chem., Int. Ed. 2008, 47, 3250-3253.
44. Meltzer, A.; Inoue, S.; Präsang, C.; Driess, M. J. Am. Chem. Soc. 2010, 132, 3038-3046
45. Jana, A.; Schulzke, C.; Roesky, H. W. J. Am. Chem. Soc. 2009, 131, 4600-4601
46. Jana, A.; Roesky, H. W.; Schulzke, C.; Samuel, P. P. Organometallics 2009, 28, 6574-6577
47. Yao, S.; Brym, M.; van Wüllen, C.; Driess, M. Angew. Chem. 2007, 119, 4237-4240
48. Angew. Chem., Int. Ed. 2007, 46, 4159-4162.
49. Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Heinicke, J.; Boese, R.; Bläser, D. J. Organomet. Chem. 1996, 521, 211-220
50. Haaf, M.; Schmiedl, A.; Schmedake, T. A.; Powell, D. R.; Millevolte, A. J.; Denk, M.; West, R. J. Am. Chem. Soc. 1998, 120, 12714-12719
51. Xiong, Y.; Yao, S.; Brym, M.; Driess, M. Angew. Chem. 2007, 119, 4595-4597
52. Angew. Chem., Int. Ed. 2007, 46, 4511-4513.
53. Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Slootweg, J. C. Chem. Commun. 2000, 1427-1428
54. Antolini, F.; Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Slootweg, J. C. Dalton. Trans. 2004, 3288-3294
55. Xiong, Y.; Yao, S.; Driess, M. Organometallics 2009, 28, 1927-1933
56. Präsang, C.; Stoelzel, M.; Inoue, S.; Meltzer, A.; Driess, M. Angew. Chem. 2010, 122, 10199-10202
57. Angew. Chem., Int. Ed. 2010, 49, 10002-10005.
58. Xiong, Y.; Yao, S.; Driess, M. Chem.-Eur. J. 2009, 15, 5545-5551
59. Xiong, Y.; Yao, S.; Driess, M. Organometallics 2010, 29, 987-990
60. Clendenning, S. B.; Gehrhus, B.; Hitchcock, P. B.; Nixon, J. F. Chem. Commun. 1999, 2451-2452
61. Gehrhus, B.; Hitchcock, P. B. Organometallics 2004, 23, 2848-2849
62. Ishida, S.; Iwamoto, T.; Kira, M. Organometallics 2010, 29, 5526-5534
63. Heinicke, J.; Gehrhus, B. J. Organomet. Chem. 1992, 423, 13-21
64. Haaf, M.; Hayashi, R.; West, R. J. Chem. Soc., Chem. Commun. 1994, 33-34
65. Schmedake, T. A.; Haaf, M.; Paradise, B. J.; Millevolte, A. J.; Powell, D.; West, R. J. Organomet. Chem. 2001, 636, 17-25
66. Yang, W.; Fu, H.; Wang, H.; Chen, M.; Ding, Y.; Roesky, H. W.; Jana, A. Inorg. Chem. 2009, 48, 2058-2060
67. Li, J.; Merkel, S.; Henn, J.; Meindl, K.; Döring, A.; Roesky, H. W.; Ghadwal, R. S.; Stalke, D. Inorg. Chem. 2010, 49, 775-777
68. Tavčar, G.; Sen, S. S.; Azhakar, R.; Thorn, A.; Roesky, H. W. Inorg. Chem. 2010, 49, 10199-10202
69. Meltzer, A.; Präsang, C.; Driess, M. J. Am. Chem. Soc. 2009, 131, 7232-7233
70. Gehrhus, B.; Hitchcock, P. B.; Lappert, M. F.; Maciejewski, H. Organometallics 1998, 17, 5599-5601
71. Ghadwal, R. S.; Roesky, H. W.; Merkel, S.; Stalke, D. Chem.-Eur. J. 2010, 16, 85-88
72. Azhakar, R.; Tavčar, G.; Roesky, H. W.; Hey, J.; Stalke, D. Eur. J. Inorg. Chem. 2011, 475-477
73. Jana, A.; Samuel, P. P.; Tavčar, G.; Roesky, H. W.; Schulzke, C. J. Am. Chem. Soc. 2010, 132, 10164-10170
74. Barbe, G.; Pelletier, G.; Charette, A. B. Org. Lett. 2009, 11, 3398-3401
75. Miller, K. L.; Williams, B. N.; Benitez, D.; Carver, C. T.; Ogilby, K. R.; Tkatchouk, E.; Goddard, W. A., III; Diaconescu, P. L. J. Am. Chem. Soc. 2010, 132, 342-355
76. Duhovic, S.; Monreal, M. J.; Diaconescu, P. L. Inorg. Chem. 2010, 49, 7165-7169
77. Feller, M.; Ben-Ari, E.; Iron, M. A.; Diskin-Posner, Y.; Leitus, G.; Shimon, L. J. W.; Konstantinovski, L.; Milstein, D. Inorg. Chem. 2010, 49, 1615-1625
78. Zeng, G.; Guo, Y.; Li, S. Inorg. Chem. 2009, 48, 10257-10263
79. Kocher, N.; Henn, J.; Gostevskii, B.; Kost, I.; Kalikhman, I.; Engels, B.; Stalke, D. J. Am. Chem. Soc. 2004, 126, 5563-5568
80. Ott, H.; Pieper, U.; Leusser, D.; Flierler, U.; Henn, J.; Stalke, D. Angew. Chem. 2009, 121, 3022-3026
81. Angew. Chem., Int. Ed. 2009, 48, 2978-2982.
82. Macchi, P. Angew. Chem. 2009, 121, 5905-5907
83. Angew. Chem., Int. Ed. 2009, 48, 5793-5795.
84. Chandrasekhar, V.; Azhakar, R. CrystEngComm 2005, 7, 346-349
85. Chandrasekhar, V.; Azhakar, R.; Murugesapandian, B.; Senapati, T.; Bag, P.; Pandey, M. D.; Maurya, S. K.; Goswami, D. Inorg. Chem. 2010, 48, 4008-4016
86. Chandrasekhar, V.; Azhakar, R.; Bickley, J.; Steiner, A. Chem. Commun. 2005, 459-461
87. Chandrasekhar, V.; Azhakar, R.; Zacchini, S.; Bickley, J.; Steiner, A. Inorg. Chem. 2005, 44, 4608-4615
88. Chandrasekhar, V.; Azhakar, R.; Andavan, G. T. S.; Krishnan, V.; Zacchini, S.; Bickley, J.; Steiner, A.; Butcher, R. J.; Kögerler, P. Inorg. Chem. 2003, 42, 5989-5998
89. Stalke, D. Chem. Soc. Rev. 1998, 27, 171-178
90. Kottke, T.; Stalke, D. J. Appl. Crystallogr. 1993, 26, 615-619
91. Schulz, T.; Meindl, K.; Leusser, D.; Stern, D.; Graf, J.; Michaelsen, C.; Ruf, M.; Sheldrick, G. M.; Stalke, D. J. Appl. Crystallogr. 2009, 42, 885-891
92. SAINT; Bruker AXS Inc.: Madison, WI, 2000.
93. Sheldrick, G. M. SADABS; Universität Göttingen: Göttingen, Germany, 2000.
94. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122
95. Frisch, M. J. Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004, (for complete list of authors see Supporting Information).
96. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100
97. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824
98. Perdew, J. P. Phys. Rev. B 1986, 34, 7406-7406
99. Schäfer, A.; Horn, H.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571-2577
100. Dunlap, B. I. J. Chem. Phys. 1983, 78, 3140-3142
101. Dunlap, B. I. J. Mol. Struct. (Theochem) 2000, 529, 37-40
102. http://www.chemcraftprog.com/index.html.