12,15-Dichloro[3.0]orthometacyclophane: A highly strained biphenylophane

Journal of the American Chemical Society

Volumn 120, Issue 14, 1998, Pages 3371-3375

  Van Eis, Maurice J ^a   De Kanter, Franciscus J J ^a   De Wolf, Willem H ^a   Bickelhaupt, Friedrich ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

12,15 DICHLORO[3.0]ORTHOMETACYCLOPHANE; BIPHENYLOPHANE DERIVATIVE; METACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DRUG CONFORMATION; DRUG SYNTHESIS;

EID: 0032522193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973876n     Document Type: Article

References (26)

1. (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Engl. 1996, 35, 2085.
2. (a) Bodwell, G. J. Angew. Chem. 1996, 108, 2221; Angew. Chem., Int. Ed. Engl. 1996, 35, 2085.
3. (b) Okuyama, M.; Tsuji, T. Angew. Chem. 1997, 109, 1157; Angew. Chem., Int. Ed. Engl. 1997, 36, 1085.
4. (b) Okuyama, M.; Tsuji, T. Angew. Chem. 1997, 109, 1157; Angew. Chem., Int. Ed. Engl. 1997, 36, 1085.
5. Kostermans, G. B. M.; Van Dansik, P.; De Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1987, 109, 7887.
6. Van Straten, J. W.; De Wolf, W. H.; Bickelhaupt, F. Tetrahedron Lett. 1977, 4667.
7. Wijsman, G. W.; Van Es, D. S., De Wolf, W. H.; Bickelhaupt, F. Angew. Chem. 1993, 105, 739. Angew. Chem., Int. Ed. Engl. 1993, 32, 726
8. Wijsman, G. W.; Van Es, D. S., De Wolf, W. H.; Bickelhaupt, F. Angew. Chem. 1993, 105, 739. Angew. Chem., Int. Ed. Engl. 1993, 32, 726
9. Van Es, D. S.; Egberts, A.; Nkrumah, S.; De Nijs, H.; De Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1997, 119, 615.
10. Tobe, Y.; Kawaguchi, M.; Kakiuchi, K.; Naemura, K. J. Am. Chem. Soc. 1993, 115, 1173.
11. Vögtle, F. Chem. Ber. 1969, 102, 1449.
12. Bodwell, G., Ernst, L.; Haenel, M. W.; Hopf, H. Angew. Chem. 1989, 101, 509; Angew. Chem., Int. Ed. Engl. 1989, 28, 455.
13. Bodwell, G., Ernst, L.; Haenel, M. W.; Hopf, H. Angew. Chem. 1989, 101, 509; Angew. Chem., Int. Ed. Engl. 1989, 28, 455.
14. Bickelhaupt, F.; De Wolf, W. H. In Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press Ltd: London, 1993; Vol. 3, p 185.
15. 4
16. MM2 calculations were performed using CSC Chem3D Plus 3.1.1, Serial Number 460045, licensed to the Vrije Universiteit.
17. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209. The calculations were performed using MOPAC 93 (QCPE no. 445).
18. (a) The density functional calculations were performed using the Amsterdam Density Functional (ADF) program, version 2.3.3, developed by Baerends et al.
19. (b) Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
20. (c) Te Velde, G.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
21. Fonseca Guerra, C.; Visser, O.; Snijders, J. G.; Te Velde, G.; Baerends E. J. In Methods and Techniques for Computational Chemistry; Clementi, E., Corongiu, G., Eds.; STEF: Cagliari, Italy, 1995; p 305.
22. Jenneskens, L. W.; Klamer, J. C.; de Boer, H. J. R.; de Wolf, W. H.; Bickelhaupt, F.; Stam, C. H. Angew. Chem. 1984, 96, 236; Angew. Chem., Int. Ed. Engl. 1984, 23, 238.
23. Jenneskens, L. W.; Klamer, J. C.; de Boer, H. J. R.; de Wolf, W. H.; Bickelhaupt, F.; Stam, C. H. Angew. Chem. 1984, 96, 236; Angew. Chem., Int. Ed. Engl. 1984, 23, 238.
24. 16).
25. Benson, S. W. Thermochemical Kinetics, 2nd ed.; Wiley: New York, 1976.
26. Concerning the nomenclature, see: Vögtle, F.; Neumann, P. Tetrahedron 1970, 26, 5847.