The transfer of tin and germanium atoms from n-heterocyclic stannylenes and germylenes to diazadienes

Chemistry - A European Journal

Volumn 12, Issue 4, 2006, Pages 1162-1173

  Gans Eichler, Timo ^b   Gudat, Dietrich ^a   Nättinen, Kalle ^b,c   Nieger, Martin ^b  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF BONN   (Germany)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Atom transfer; Carbenoids; Germanium stannanes; Triplet states

Indexed keywords

AMINATION; CHARGE TRANSFER; GERMANIUM; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL); TIN; X RAY DIFFRACTION ANALYSIS;

ATOM TRANSFER; CARBENOIDS; GERMANIUM STANNANES; TRIPLET STATES;

NITROGEN COMPOUNDS;

EID: 31344453757     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500576     Document Type: Article

References (48)

1. D. Bourissou, O. Guerret, F. P. Gabbai, G. Bertrand, Chem. Rev. 2000, 100, 39.
2. W. A. Herrmann, Angew, Chem. 2002, 114, 1342;
3. Angew. Chem. Int. Ed. 2002, 41, 1291;
4. V. Nair, S. Bindu, V. Sreekumar, Angew. Chem. 2004, 116, 5240;
5. Angew. Chem. Int. Ed. 2004, 43, 5130.
6. A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991. 113, 361.
7. M. Haaf, T. A. Schmedake, R. West, Acc. Chem. Res. 2000, 33, 704;
8. N. J. Hill, R. West, J. Organomet. Chem, 2004, 689, 4165.
9. O. Kühl, Coord, Chem. Rev. 2004, 248, 411.
10. H. Braunschweig, B. Gehrhus, P. B. Hitchcock, M. F. Lappert, Z. Anorg. Allg. Chem. 1995, 621, 1922:
11. J. Heinicke, A. Oprea, M. K. Kindermann, T. Karpati, L. Nyulaszi, T. Veszpremi, Chem. Eur. J. 1998, 4, 541.
12. M. F. Lappert, P. P. Power, A. R. Sanger, R. C. Srivastava, Metal and Metalloid Amides: Ellis - Horwood, Chichester, 1980.
13. T. Gans-Eichler, D. Gudat, M. Nieger, Angew. Chem. 2002, 114, 1966;
14. Angew. Chem. Int. Ed. 2002, 41, 1888.
15. M. Haaf, A. Schmiedl, T. A. Schmedake, D. R. Powell, A. J. Millevolte, M. Denk, R. West, J. Am. Chem. Soc. 1998, 120, 12714.
16. S. Schweiger, G. Rauhut, J. Phys. Chem. A 2003, 107, 9668.
17. a) Y. Zhou, D. S. Richeson, J. Am. Chem. Soc. 1996, 118, 10850;
18. b) S. R. Foley, Y. Zhou, G. P. A. Yap, D. S. Richeson, Inorg. Chem. 2000, 39, 924.
19. H. tom Dieck, K. D. Franz, Angew. Chem. 1975, 87, 244:
20. Angew. Chem. Int. Ed. Engl. 1975, 14, 249:
21. K. D. Franz, H. tom Dieck, K. S. Ostoja Starzewski, F. Hohmann, Tetrahedron 1975, 31, 1465;
22. M. G. Gardiner, G. R. Hanson, M. J. Henderson, F. C. Lee, C. L. Raston, Inorg. Chem. 1994, 33, 2456;
23. M. G. Gardiner, C. L. Raston, B. W. Skelton, A. H. White, Inorg. Chem. 1997, 36, 2795;
24. G. A. Abakumov, V. K. Cherkasov, A. V. Piskunov, N. O. Druzhkov, Dokl. Chem. 2004, 399, 223.
25. Computed relative energies of singlet and triplet states of the stannylene 1c and the diazadiene 3c at the same level of theory disclosed this combination to be energetically more favorable than the addition of a singlet stannylene to a triplet diazadiene.
26. Y. Apeloig, R. Pauncz, M. Karni, R. West, W. Steiner, D. Chapman, Organometallics 2003, 22, 3250.
27. -1 above that of the singlet ground state and requires thus a similar excitation energy as in the carbenes IC.
28. H. Grützmacher, F. Breher, Angew. Chem. 2002, 114, 4178;
29. Angew. Chem. Int. Ed. 2002, 41, 4006;
30. W. W. Schoeller, C. Begemann, E. Niccke, D. Gudat, J. Phys. Chem. A 2001, 105, 10731, and references therein.
31. Even if no crossing of the triplet and singlet, hypersurfaces will occur in case that a more sophisticated computational treatment discloses a singlet ground state for the spirocycles, both hypersurfaces remain still close in energy and conversion of a singlet into a triplet state during a reaction of a stannylene with a diazadiene may remain feasible with a certain probability.
32. H. tom Dieck, M. Svoboda, T. Greiser, Z. Naturforsch. 1981, 3613, 823;
33. H. A. Zhong, J. A. Labinger, J. E. Bercaw, J. Am. Chem, Soc. 2002, 124, 1378.
34. Mean value and standard deviations of the results of a query in the CSD database for acyclic compounds with the structural element NH-C=C-NH.
35. A. J. Arduengo, D. A. Dixon, K. K. Kumahiro, C. Lee, W. P. Power, K. W. Zilm, J. Am. Chem. Soc. 1994, 116, 6361;
36. R. West, J. J. Buffy, M. Haaf, T. Müller, B. Gehrhus, M. F. Lappert, Y. Apeloig, J. Am. Chem. Soc. 1998, 120, 1639.
37. W. A. Herrmann, M. Denk, J. Behm, W. Scherer, F. R. Klingan, H. Bock, B. Solouki, M. Wagner, Angew. Chem. 1992, 104, 1489;
38. Angew. Chem. Int. Ed. Engl. 1992, 31, 1485.
39. 3J-(H,H) suggests a transoid conformation of the C=N double bonds.
40. C. L. Perrin, T. J. Dwyer, Chem. Rev. 1990, 90, 935.
41. S. Forsen, R. A. Huffman, J. Chem. Phys. 1963, 39, 2892;
42. R. A. Huffman, S. Forsen, Prog. Nucl. Magn. Reson. Spectrosc. 1966, 2, 15.
43. M. Saito, N. Tokitoh, R. Okazaki, J. Am. Chem. Soc. 2004, 126, 15 572.
44. DFT calculations were performed using the Gaussian suite of programs: Gaussian 98 (Rev. A.7). M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian, Inc., Pittsburgh, PA. 1998.
45. NBO 5.0: E. D. Glendening, J. K. Badenhoop, A. E. Reed, J. E. Carpenter, J. A. Bohmann, C. M. Morales, F. Weinhold, Theoretical Chemistry Institute, University of Wisconsin,: Madison, WI, 2001; http://www.chem.wisc.edu/~nbo5.
46. J. J. Led, H. Gesmar, J. Magn. Res. 1982, 49, 444.
47. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, A46, 467.
48. G. M. Sheldrick, University of Göttingen, Göttingen (Germany), 1997.