A highly reactive triboracyclobutane and its dianion: Two-electron homoaromatics with nonclassical and classical σ skeletons

Organometallics

Volumn 22, Issue 8, 2003, Pages 1594-1596

  Amseis, Peter ^a   Mesbah, Wahid ^a   Präsang, Carsten ^a   Hofmann, Matthias ^b   Geiseler, Gertraud ^a   Massa, Werner ^a   Berndt, Armin ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL BONDS; CRYSTAL STRUCTURE; ELECTRONS; LITHIUM COMPOUNDS; NEGATIVE IONS; THERMAL EFFECTS;

DIANION; DILITHIUM SALT; TRIBORACYCLOBUTANE; TWO ELECTRON HOMOAROMATICS;

ORGANIC COMPOUNDS;

EID: 0038682041     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om021046z     Document Type: Article

References (27)

1. Korkin, A. A.; Schleyer, P. v. R.; McKee, M. L. Inorg. Chem. 1995, 34, 961.
2. McKee, M. L. Inorg. Chem. 1999, 38, 321.
3. Berndt, A.; Steiner, D.; Schweikart, D.; Balzereit, C.; Menzel, M.; Winkler, H.-J.; Mehle, S.; Unverzagt, M.; Happel, T.; Schleyer, P. v. R.; Subramanian, G.; Hofmann, M. Adv. Boron Chem. 1997, 61.
4. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.: Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
5. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372, 5648.
6. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
7. Steiner, D.; Winkler, H.-J.; Balzereit, C.; Happel, T.; Hofmann, M.; Subramanian, G.; Schleyer, P. v. R.; Massa, W.; Berndt, A. Angew. Chem. 1996, 108, 2123
8. Steiner, D.; Winkler, H.-J.; Balzereit, C.; Happel, T.; Hofmann, M.; Subramanian, G.; Schleyer, P. v. R.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1990.
9. (a) Scheschkewitz, D.; Ghaffari, A.; Amseis, P.; Unverzagt, M.; Subramanian, G.; Hofmann, M.; Schleyer, P. v. R.; Schaefer, H. F., III; Geiseler, G.; Massa, W.; Berndt, A., Angew. Chem. 2000, 112, 1329
10. Scheschkewitz, D.; Ghaffari, A.; Amseis, P.; Unverzagt, M.; Subramanian, G.; Hofmann, M.; Schleyer, P. v. R.; Schaefer, H. F., III; Geiseler, G.; Massa, W.; Berndt, A., Angew. Chem., Int. Ed. 2000, 39, 1272.
11. (b) Unverzagt, M.; Subramanian, G.; Hofmann, M.; Schleyer, P. v. R.; Berger, S.; Harms, K.; Massa, W.; Berndt, A. Angew. Chem. 1997 109, 1567
12. Unverzagt, M.; Subramanian, G.; Hofmann, M.; Schleyer, P. v. R.; Berger, S.; Harms, K.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. 1997, 36, 1469.
13. 3, 25 °C): δ 37 (2B), 62.
14. 8]toluene): -80 °C, δ 10, 13, 16, 21, 40, 51; 25 °C, δ, 14, 22, 42, 54; 65 °C, δ 16, 24, 48.
15. 2, SHELXL-97); anisotropic displacement parameters were used for all non-H atoms in the final cycles, and H atoms were treated by a mixture of independent (H1, H2a, H2b) and constrained refinement. R1 = 0.0523 (I > 2σ(I)), and wR2 = 0.1489 (all data). Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-175173. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (fax, int. code + 44(1223)336-033; e-mail, deposit@ccdc.cam.ac.uk).
16. Sheldrick, G. M. SHELX-97, Programs for the Solution and Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997.
17. Sekiguchi, A.; Matsuo, T.; Watanabe, H., J. Am. Chem. Soc. 2000, 122, 5652
18. Sekiguchi, A.; Tanaka, M.; Matsuo, T.; Watanabe, H., Angew. Chem. 2001, 113, 1721
19. Sekiguchi, A.; Tanaka, M.; Matsuo, T.; Watanabe, H., Angew. Chem., Int. Ed. Engl. 2001, 40, 1675.
20. 2- over π coordination.
21. Bradenburg, K. Diamond 2.1c; Crystal Impact GbR, Bonn, Germany, 1999.
22. 8]toluene, -105 °C) δ 14, 25, 29.
23. Menzel, M.; Winkler, H.-J.; Ablelom, T.; Steiner, D.; Fau, S.; Frenking, G.; Massa, W.; Berndt, A. Angew. Chem. 1995, 107, 1476
24. Menzel, M.; Winkler, H.-J.; Ablelom, T.; Steiner, D.; Fau, S.; Frenking, G.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1340.
25. Pilz, M.; Allwohn, J.; Massa, W.; Berndt, A. Angew. Chem. 1990, 102, 436
26. Pilz, M.; Allwohn, J.; Massa, W.; Berndt, A. Angew. Chem., Int. Ed. Engl. 1990, 29, 399.
27. Budzelaar, P. H. M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 3967, and literature cited therein.