Conversion of a singlet silylene to a stable biradical

Angewandte Chemie - International Edition

Volumn 52, Issue 6, 2013, Pages 1801-1805

  Mondal, Kartik Chandra ^a   Roesky, Herbert W ^a   Schwarzer, Martin C ^b   Frenking, Gernot ^b   Tkach, Igor ^c   Wolf, Hilke ^a   Kratzert, Daniel ^a   Herbst Irmer, Regine ^a   Niepötter, Benedikt ^a   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

^c MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

biradicals; cyclic alkyl(amino)carbenes; EPR spectroscopy; N heterocyclic carbenes; singlet silylenes

Indexed keywords

BIRADICALS; CARBENES; EPR SPECTROSCOPY; N-HETEROCYCLIC CARBENES; SILYLENES;

ACTIVATION ANALYSIS;

ORGANIC COMPOUNDS;

CARBENE; CARBON; DRUG DERIVATIVE; FREE RADICAL; HETEROCYCLIC COMPOUND; HYDROGEN; METHANE; SILICON DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; QUANTUM THEORY; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CARBON; CRYSTALLOGRAPHY, X-RAY; FREE RADICALS; HETEROCYCLIC COMPOUNDS; HYDROGEN; METHANE; MOLECULAR CONFORMATION; QUANTUM THEORY; SILICON COMPOUNDS; THERMODYNAMICS;

EID: 84872743375     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201204487     Document Type: Article

References (47)

1. M. B. Smith, J. March, Advanced Organic Chemistry, 5 th ed., Wiley, New York, 2001.
2. E. Niecke, A. Fuchs, F. Baumeister, M. Nieger, W. W. Schoeller, Angew. Chem. 1995, 107, 640-642
3. Angew. Chem. Int. Ed. Engl. 1995, 34, 555-557.
4. C. Cui, M. Brynda, M. M. Olmstead, P. P. Power, J. Am. Chem. Soc. 2004, 126, 6510-6511.
5. H. Cox, P. B. Hitchcock, M. F. Lappert, L. J.-M. Pierssens, Angew. Chem. 2004, 116, 4600-4604
6. Angew. Chem. Int. Ed. 2004, 43, 4500-4504.
7. J.-B. Bourg, A. Rodriguez, D. Scheschkewitz, H. Gornitzka, D. Bourissou, G. Bertrand, Angew. Chem. 2007, 119, 5843-5847
8. Angew. Chem. Int. Ed. 2007, 46, 5741-5745.
9. K. Takeuchi, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 2011, 133, 12478-12481.
10. T. Nozawa, M. Nagata, M. Ichinohe, A. Sekiguchi, J. Am. Chem. Soc. 2011, 133, 5773-5775.
11. P. P. Power, Chem. Rev. 2003, 103, 789-810.
12. V. Ya. Lee, A. Sekiguchi, Acc. Chem. Res. 2007, 40, 410-419.
13. H. Grützmacher, F. Breher, Angew. Chem. 2002, 114, 4178-4184
14. Angew. Chem. Int. Ed. 2002, 41, 4006-4011.
15. A. Rajca, K. Lu, S. Rajca, C. R. Ross II, Chem. Commun. 1999, 1249-1250.
16. N. Roques, P. Gerbier, U. Schatzschneider, J.-P. Sutter, P. Guionneau, J. Vidal-Gancedo, J. Veciana, E. Rentschler, C. Guérin, Chem. Eur. J. 2006, 12, 5547-5562.
17. C. Riplinger, J. P. Y. Kao, G. M. Rosen, V. Kathirvelu, G. R. Eaton, S. S. Eaton, A. Kutateladze, F. Neese, J. Am. Chem. Soc. 2009, 131, 10092-10106.
18. R. S. Ghadwal, H. W. Roesky, S. Merkel, J. Henn, D. Stalke, Angew. Chem. 2009, 121, 5793-5796
19. Angew. Chem. Int. Ed. 2009, 48, 5683-5686
20. S. S. Sen, S. Khan, P. P. Samuel, H. W. Roesky, Chem. Sci. 2012, 3, 659-682
21. R. S. Ghadwal, H. W. Roesky, K. Pröpper, B. Dittrich, S. Klein, G. A. Frenking, Angew. Chem. 2011, 123, 5486-5490
22. Angew. Chem. Int. Ed. 2011, 50, 5374-5378.
23. V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. 2005, 117, 5851-5855
24. Angew. Chem. Int. Ed. 2005, 44, 5705-5709.
25. M. Kaftory, M. Kapon, M. Botoshansky, in The chemistry of Organic Silicon Compounds, Vol. 2, Part 1, (Eds.:, Z. Rappoport, Y. Apeloig,), Wiley, Chichester, 1998, chap. 5.
26. V. Ya. Lee, A. Sekiguchi, Organometallic Compounds of Low-Coordinate Si, Ge, Sn and Pb: From Phantom Species to Stable Compounds, Wiley, Chichester, 2010, chap. 5.
27. V. Lavallo, G. D. Frey, S. Kousar, B. Donnadieu, G. Bertrand, Proc. Natl. Acad. Sci. USA 2007, 104, 13569-13573.
28. J. A. Berson, in Reactive Intermediate Chemistry (Eds.:, R. A. Moss, M. S. Platz, M. Jones,), Wiley, Hoboken, 2004, chap. 5.
29. R. Kinjo, B. Donnadieu, M. A. Celik, G. Frenking, G. Bertrand, Science 2011, 333, 610-613.
30. O. Kahn, Molecular Magnetism, VCH, Weinheim, 1993.
31. F. E. Mabbs, D. J. Machin, Magnetism and Transition Metal Complexes, Chapman and Hall, London, 1973.
32. C. J. Milios, A. Vinslava, W. Wernsdorfer, A. Prescimone, P. A. Wood, S. Parsons, S. P. Perlepes, G. Christou, E. K. Brechin, J. Am. Chem. Soc. 2007, 129, 6547-6561.
33. D. Stalke, Chem. Soc. Rev. 1998, 27, 171-178
34. T. Kottke, D. Stalke, J. Appl. Crystallogr. 1993, 26, 615-619.
35. T. Schulz, K. Meindl, D. Leusser, D. Stern, J. Graf, C. Michaelsen, M. Ruf, G. M. Sheldrick, D. Stalke, J. Appl. Crystallogr. 2009, 42, 885-891.
36. SAINT, Bruker AXS Inc., Madison, Wisconsin (USA) 2000.
37. G. M. Sheldrick, SADABS, Universität Göttingen, Germany, 2000.
38. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
39. Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Phys. 2005, 123, 161103-161111
40. A. D. Becke, J. Chem. Phys. 1993, 98, 1372-1377
41. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
42. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865-3868.
43. A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577
44. F. Weigend, M. Häser, H. Patzelt, R. Ahlrichs, Chem. Phys. Lett. 1998, 294, 143-149.
45. Gaussian 09, Revision A.1, M. J. Frisch et al. Gaussian, Inc., Wallingford CT, 2009. For full reference see the Supporting Information.
46. Turbomole 6.3, COSMOLOGIC GmbH, Leverkusen
47. R. Ahlrichs, M. Baer, M. Haeser, H. Horn, C. Koelmel, Chem. Phys. Lett. 1989, 162, 165-169.