The crystal and molecular structure of 2,7-di-tert-butyl-4,5,9,10-tetraphenylbenzo[1,2,:4,5]dicyclobutadiene: An exceptionally long C-C aromatic bond

Chemical Communications

Volumn , Issue 4, 1999, Pages 319-320

  Boese, Roland ^a   Benet Buchholz, Jordi ^a   Stanger, Amnon ^b   Tanaka, Koichi ^c   Toda, Fumio ^c  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^c EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,7 DI TERT BUTYL 4,5,9,10 TETRAPHENYLBENZO[1,2,:4,5]DICYCLOBUTADIENE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

EID: 0033590675     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a809116a     Document Type: Article

References (21)

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11. See, for example, A. Bashall, V. C, Gibson, T. P. Kee, M. McPartlin, O. B. Robinson and A. Shaw, Angew. Chem., 1991, 103, 1021; Angew. Chem., Int. Ed. Engl., 1991, 30, 980; G. Parkin, Acc. Chem. Res., 1992, 25, 455; G. Parkin, Chem. Rev., 1993, 93, 887; K. Yoon, G. Parkin and A. L. Rheingold, J. Am. Chem. Soc., 1993, 114, 2210.
12. See, for example, A. Bashall, V. C, Gibson, T. P. Kee, M. McPartlin, O. B. Robinson and A. Shaw, Angew. Chem., 1991, 103, 1021; Angew. Chem., Int. Ed. Engl., 1991, 30, 980; G. Parkin, Acc. Chem. Res., 1992, 25, 455; G. Parkin, Chem. Rev., 1993, 93, 887; K. Yoon, G. Parkin and A. L. Rheingold, J. Am. Chem. Soc., 1993, 114, 2210.
13. See, for example, A. Bashall, V. C, Gibson, T. P. Kee, M. McPartlin, O. B. Robinson and A. Shaw, Angew. Chem., 1991, 103, 1021; Angew. Chem., Int. Ed. Engl., 1991, 30, 980; G. Parkin, Acc. Chem. Res., 1992, 25, 455; G. Parkin, Chem. Rev., 1993, 93, 887; K. Yoon, G. Parkin and A. L. Rheingold, J. Am. Chem. Soc., 1993, 114, 2210.
14. See, for example, A. Bashall, V. C, Gibson, T. P. Kee, M. McPartlin, O. B. Robinson and A. Shaw, Angew. Chem., 1991, 103, 1021; Angew. Chem., Int. Ed. Engl., 1991, 30, 980; G. Parkin, Acc. Chem. Res., 1992, 25, 455; G. Parkin, Chem. Rev., 1993, 93, 887; K. Yoon, G. Parkin and A. L. Rheingold, J. Am. Chem. Soc., 1993, 114, 2210.
15. See, for example, A. Bashall, V. C, Gibson, T. P. Kee, M. McPartlin, O. B. Robinson and A. Shaw, Angew. Chem., 1991, 103, 1021; Angew. Chem., Int. Ed. Engl., 1991, 30, 980; G. Parkin, Acc. Chem. Res., 1992, 25, 455; G. Parkin, Chem. Rev., 1993, 93, 887; K. Yoon, G. Parkin and A. L. Rheingold, J. Am. Chem. Soc., 1993, 114, 2210.
16. -3. CCDC 182/1129.
17. -1.
18. GAUSSIAN 94, Revision E. I, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995.
19. N. L. Frank, K. K. Baldridge and J. A. Siegel, J. Am. Chem. Soc., 1995, 117, 2102.
20. The discussion presented here for 4 regards the tetraethenyl derivative of isomer 2d. However, 2a also has a stable tetravinyl derivative. The two bond-shift isomers (i.e. 2a and 2d) also have other stable derivatives that show this isomerism, such as the tetrahydroxy and tetracyano derivatives (A. Stanger, unpublished results). These are, however, beyond the scope of this paper.
21. The agreement between the experimental and calculated structures is even better if the experimental σ value (0.005 Å for all the discussed bonds) is considered.