Synthesis, x-ray structure, and properties of a tetrabenzannelated 1,2,4,5-cyclophane

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3688-3691

  Brettreich, Michael ^a   Bendikov, Michael ^a   Chaffins, Sterling ^a   Perepichka, Dmitrii F ^a   Dautel, Olivier ^a   Duong, Hieu ^a   Helgeson, Roger ^a   Wudl, Fred ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cycloaddition; Cyclophanes; Density functional calculations; Electrochemistry; Strained molecules

Indexed keywords

STRUCTURE (COMPOSITION); SUBLIMATION; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY; X RAY ANALYSIS;

DIELS-ALDER REACTION;

AROMATIC COMPOUNDS;

1,2 DICHLOROBENZENE; 1,2,3,4 CYCLOPHANE; CYCLOPHANE DERIVATIVE; PARA XYLENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; DECOMPOSITION; PROTON NUCLEAR MAGNETIC RESONANCE; PYROLYSIS; QUANTUM MECHANICS; SYNTHESIS; THERMOGRAVIMETRY; X RAY ANALYSIS;

EID: 0037020382     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3688::AID-ANIE3688>3.0.CO;2-Q     Document Type: Article

References (68)

1. a) J. C. Wittman, P. Smith, Nature 1991, 352, 414;
2. b) M. F. Nichols, Crit. Rev. Biomed. Eng. 1994, 22, 39;
3. c) K. M. Vaeth, K. F. Jensen, Chem. Mater. 2000, 12, 1305, and references therein.
4. V. V. Kane, W. H. De Wolf, F. Bickelhaupt, Tetrahedron 1994, 50, 4575; I. V. Komarov, Russ. Chem. Rev. 2001, 70, 991; J. Reinbold, E. Sackers, T. Osswald, K. Weber, A. Weiler, T. Voss, D. Hunkler, J. Worth, L. Knothe, F. Sommer, B. von Issendorff, H. Prinzbach, Chem. Eur. J. 2002, 8, 509.
5. V. V. Kane, W. H. De Wolf, F. Bickelhaupt, Tetrahedron 1994, 50, 4575; I. V. Komarov, Russ. Chem. Rev. 2001, 70, 991; J. Reinbold, E. Sackers, T. Osswald, K. Weber, A. Weiler, T. Voss, D. Hunkler, J. Worth, L. Knothe, F. Sommer, B. von Issendorff, H. Prinzbach, Chem. Eur. J. 2002, 8, 509.
6. V. V. Kane, W. H. De Wolf, F. Bickelhaupt, Tetrahedron 1994, 50, 4575; I. V. Komarov, Russ. Chem. Rev. 2001, 70, 991; J. Reinbold, E. Sackers, T. Osswald, K. Weber, A. Weiler, T. Voss, D. Hunkler, J. Worth, L. Knothe, F. Sommer, B. von Issendorff, H. Prinzbach, Chem. Eur. J. 2002, 8, 509.
7. A. Nickon, E. F. Silversmith, Organic Chemistry: the Name Game, Pergamon, New York, 1988.
8. "Fullerenes and Related Structures": Top. Curr. Chem. 1999, 199.
9. "Cyclophanes I": Top. Curr. Chem. 1983, 113; "Cyclophanes II": Top. Curr. Chem. 1983, 115; Cyclophanes: Organic Chemistry, Vol. 45 (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983; F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, UK, 1991 (Monographs in Supramolecular Chemistry); T. Tsuji, M. Ohkita, H. Kawai, Bull. Chem. Soc. Jpn. 2002, 75, 415.
10. "Cyclophanes I": Top. Curr. Chem. 1983, 113; "Cyclophanes II": Top. Curr. Chem. 1983, 115; Cyclophanes: Organic Chemistry, Vol. 45 (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983; F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, UK, 1991 (Monographs in Supramolecular Chemistry); T. Tsuji, M. Ohkita, H. Kawai, Bull. Chem. Soc. Jpn. 2002, 75, 415.
11. "Cyclophanes I": Top. Curr. Chem. 1983, 113; "Cyclophanes II": Top. Curr. Chem. 1983, 115; Cyclophanes: Organic Chemistry, Vol. 45 (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983; F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, UK, 1991 (Monographs in Supramolecular Chemistry); T. Tsuji, M. Ohkita, H. Kawai, Bull. Chem. Soc. Jpn. 2002, 75, 415.
12. "Cyclophanes I": Top. Curr. Chem. 1983, 113; "Cyclophanes II": Top. Curr. Chem. 1983, 115; Cyclophanes: Organic Chemistry, Vol. 45 (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983; F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, UK, 1991 (Monographs in Supramolecular Chemistry); T. Tsuji, M. Ohkita, H. Kawai, Bull. Chem. Soc. Jpn. 2002, 75, 415.
13. "Cyclophanes I": Top. Curr. Chem. 1983, 113; "Cyclophanes II": Top. Curr. Chem. 1983, 115; Cyclophanes: Organic Chemistry, Vol. 45 (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983; F. Diederich, Cyclophanes, Royal Society of Chemistry, Cambridge, UK, 1991 (Monographs in Supramolecular Chemistry); T. Tsuji, M. Ohkita, H. Kawai, Bull. Chem. Soc. Jpn. 2002, 75, 415.
14. S. Liu, Y. J. Lu, M. M. Kappes, J. A. Ibers, Nature 1991, 254, 408.
15. K. C. Dewhirst, D. J. Cram, J. Am. Chem. Soc. 1958, 80, 3115.
16. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
17. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
18. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
19. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
20. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
21. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
22. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
23. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
24. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
25. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
26. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
27. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
28. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
29. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
30. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
31. C. W. Chan, H. N. C. Wong, J. Am. Chem. Soc. 1985, 107, 4790; M. Psiorz, H. Hopf, Angew. Chem. 1982, 94, 639; Angew. Chem. Int. Ed. Engl. 1982, 21, 623; N. Jacobson, V. Boekelheide, Angew. Chem. 1978, 90, 49; Angew. Chem. Int. Ed. Engl. 1978, 17, 46; M. Stöbbe, O. Reiser, R. Näder, A. de Meijere, Chem. Ber. 1987, 120, 1667; T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 716; Angew. Chem. Int. Ed. Engl. 1988, 27, 705; Erratum: T. Wong, S. S. Cheung, H. N. C. Wong, Angew. Chem. 1988, 100, 1242; Angew. Chem. Int. Ed. Engl. 1988, 27, 1200; C. W. Chang, H. N. C. Wong, J. Am. Chem. Soc. 1988, 110, 462;H. Buchholz, A. de Meijere, Synlett 1993, 253; O. Reiser, S. Reichow, A. de Meijere, Angew. Chem. 1987, 99, 1285; Angew. Chem. Int. Ed. Engl. 1987, 26, 1277; H.-F. Grützmacher, W. Husemann, Tetrahedron Lett. 1985, 26, 2431; Y.-H. Lai, S.-M. Lee, J. Org. Chem. 1988, 53, 4472; M. Wittek, F. Vögtle, G. Stühler, A. Mannschreck, B. M. Lang, H. Irngartinger, Chem. Ber. 1983, 116, 207.
32. Z.-Z. Yang, B. Kova, E. Heilbronner, J. Lecoultre, C. W. Chan, H. N. C. Wong, H. Hopf, F. Vögtle, Helv. Chim. Acta, 1987, 70, 299.
33. The largest number of unsaturated bridges reported is three ethenes: V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1973, 95, 3201; V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1970, 92, 3512;V. Boekelheide, W. Schmidt, Chem. Phys. Lett. 1972, 17, 410; H. Hopf, C. Mlynek, J. Org. Chem. 1990, 55, 1361.
34. The largest number of unsaturated bridges reported is three ethenes: V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1973, 95, 3201; V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1970, 92, 3512;V. Boekelheide, W. Schmidt, Chem. Phys. Lett. 1972, 17, 410; H. Hopf, C. Mlynek, J. Org. Chem. 1990, 55, 1361.
35. The largest number of unsaturated bridges reported is three ethenes: V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1973, 95, 3201; V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1970, 92, 3512;V. Boekelheide, W. Schmidt, Chem. Phys. Lett. 1972, 17, 410; H. Hopf, C. Mlynek, J. Org. Chem. 1990, 55, 1361.
36. The largest number of unsaturated bridges reported is three ethenes: V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1973, 95, 3201; V. Boekelheide, R. A. Hollins, J. Am. Chem. Soc. 1970, 92, 3512;V. Boekelheide, W. Schmidt, Chem. Phys. Lett. 1972, 17, 410; H. Hopf, C. Mlynek, J. Org. Chem. 1990, 55, 1361.
37. T. Kappe, D. Pocivalnik, Heterocycles 1983, 20, 1367; T. Kappe, W. Lube, Angew. Chem. 1971, 83, 967; Angew. Chem. Int. Ed. Engl. 1971, 10, 925; W. Friedrichsen, T. Kappe, A. Böttcher, Heterocycles 1982, 19, 1083; K. T. Potts, M. Sorm, J. Org. Chem. 1972, 37, 1422.
38. T. Kappe, D. Pocivalnik, Heterocycles 1983, 20, 1367; T. Kappe, W. Lube, Angew. Chem. 1971, 83, 967; Angew. Chem. Int. Ed. Engl. 1971, 10, 925; W. Friedrichsen, T. Kappe, A. Böttcher, Heterocycles 1982, 19, 1083; K. T. Potts, M. Sorm, J. Org. Chem. 1972, 37, 1422.
39. T. Kappe, D. Pocivalnik, Heterocycles 1983, 20, 1367; T. Kappe, W. Lube, Angew. Chem. 1971, 83, 967; Angew. Chem. Int. Ed. Engl. 1971, 10, 925; W. Friedrichsen, T. Kappe, A. Böttcher, Heterocycles 1982, 19, 1083; K. T. Potts, M. Sorm, J. Org. Chem. 1972, 37, 1422.
40. T. Kappe, D. Pocivalnik, Heterocycles 1983, 20, 1367; T. Kappe, W. Lube, Angew. Chem. 1971, 83, 967; Angew. Chem. Int. Ed. Engl. 1971, 10, 925; W. Friedrichsen, T. Kappe, A. Böttcher, Heterocycles 1982, 19, 1083; K. T. Potts, M. Sorm, J. Org. Chem. 1972, 37, 1422.
41. T. Kappe, D. Pocivalnik, Heterocycles 1983, 20, 1367; T. Kappe, W. Lube, Angew. Chem. 1971, 83, 967; Angew. Chem. Int. Ed. Engl. 1971, 10, 925; W. Friedrichsen, T. Kappe, A. Böttcher, Heterocycles 1982, 19, 1083; K. T. Potts, M. Sorm, J. Org. Chem. 1972, 37, 1422.
42. Compound 4 should be formed as a mixture of syn and anti isomers; the relative ratio of syn:anti cannot be determined on the basis of NMR spectroscopy (see Supporting Information). We speculate the anti isomer for compound 4 to be preferentially formed as a result of 1) steric repulsion between two phenyl substituents (located on opposite sides of the saddle-shaped dibenzocyclooctatetraenene ring and 2) minimization of dipole-dipole interactions of the lactam carbonyls.
43. Although a single isomer is shown for compounds 5 and 6, one cannot say with certainty if it is the anti isomer (as shown). Chromatographic isolation of 5 and 6 produces a single isomer, as evidenced by NMR spectroscopy. However, final structural determination will have to rest with X-ray crystallography. It is possible that recrystallization of 4, prior to pyrolysis, allowed selection of only one isomer, which could then only produce a single isomer of 5 (and hence 6).
44. H. N. C. Wong, P. J. Garratt, F. Sondheimer, J. Am. Chem. Soc. 1974, 96, 5604; A. Orita, D. Hasegawa, T. Nakano, J. Otera, Chem. Eur. J. 2002, 8, 2000. Some new routes for the synthesis of the dibenzocyclooctadiyne are published elsewhere (S. Chaffins, M. Brettreich, F. Wudl, Synthesis 2002, 1191).
45. H. N. C. Wong, P. J. Garratt, F. Sondheimer, J. Am. Chem. Soc. 1974, 96, 5604; A. Orita, D. Hasegawa, T. Nakano, J. Otera, Chem. Eur. J. 2002, 8, 2000. Some new routes for the synthesis of the dibenzocyclooctadiyne are published elsewhere (S. Chaffins, M. Brettreich, F. Wudl, Synthesis 2002, 1191).
46. H. N. C. Wong, P. J. Garratt, F. Sondheimer, J. Am. Chem. Soc. 1974, 96, 5604; A. Orita, D. Hasegawa, T. Nakano, J. Otera, Chem. Eur. J. 2002, 8, 2000. Some new routes for the synthesis of the dibenzocyclooctadiyne are published elsewhere (S. Chaffins, M. Brettreich, F. Wudl, Synthesis 2002, 1191).
47. 2-. CCDC-184166 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit @ccdc.cam.ac.uk).
48. a) R. G. Parr, W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989;
49. b) W. Koch, M. C. Holthausen, A Chemist's guide to density functional theory, Wiley-VCH, Weinheim, 2000.
50. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
51. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
52. HF/3-21G* was recently proposed to be very accurate for predicting geometries of series-strained cyclophanes: R. A. Pascal, Jr. J. Phys. Chem. A 2001, 105, 9040.
53. All calculations used: Gaussian 98 (Revision 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, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
54. 2h symmetry.
55. The perspective in Figure 1 b, which shows a wider distance between the protons at C9′ and C17′ than the carbon atoms to which they are bonded, is misleading since the actual positions were not determined from the data and are an artifact resulting from hydrogen atom placement by the program.
56. 4](1,2,4,5)cyclophane (A. W. Hanson, Acta Crystallogr Sect. B 1977, 33, 2003) is very similar to 1: the separation of the central carbon atoms of the two rings is 2.950 Å, and that between the two strained ring protons is 2.919 Å (calcd value). The dihedral angle between the C-C bonds in the benzene moiety is 12.2°.
57. GIAO-B3LYP/6-311 + G(d, p)//B3LYP/6-31 calculations corrected for the chemical shift of benzene (δ = 134.8 calcd, 128.0 ppm exptl) predict chemical shifts of δ = 141.4, 147.8, 148.3, 125.0, and 126.6 ppm for C9, C8, C6, C5, and C4, respectively, which allows an assignment of the experimentally observed resonance at δ = 139.3 ppm to the C9 carbon atom.
58. V. Boekelheide, Top. Curr. Chem. 1983, 113, 110.
59. 3 in anisole and nitrobenzene, respectively.
60. R. C. Haddon, Science 1993, 261, 1545.
61. Q. Xie, E. Pérez-Cordero, L. Echegoyen, J. Am. Chem. Soc. 1992, 114, 3978.
62. G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion, Chem. Eur. J. 1999, 5, 1823; G. J. Bodwell, J. J. Fleming, M. R. Mannion, D. O. Miller, J. Org. Chem. 2000, 65, 5360.
63. G. J. Bodwell, J. N. Bridson, T. J. Houghton, J. W. J. Kennedy, M. R. Mannion, Chem. Eur. J. 1999, 5, 1823; G. J. Bodwell, J. J. Fleming, M. R. Mannion, D. O. Miller, J. Org. Chem. 2000, 65, 5360.
64. 6](1,2,3,4,5,6)cyclophane) is the most strained cyclophane (see ref. [30]). However, by symmetry, its benzene rings are constrained to be nearly planar (for X-ray analysis, see A. W. Hanson, T. S. Cameron, J. Chem. Res. 1980, 10, 4201) and its reactivity with TCNE was not reported.
65. Y. Sekine, V. Boekelheide, J. Am. Chem. Soc. 1981, 103, 1777.
66. G. J. Bodwell, private communication.
67. T.-L. Chan, T. C. W. Mak, C.-D. Poon, C. Wong, J. H. Jia, L. L. Wang, Tetrahedron 1986, 42, 655; Y.-M. Man, T. C. W. Mak, H. N. C. Wong, J. Org. Chem. 1990, 55, 3214.
68. T.-L. Chan, T. C. W. Mak, C.-D. Poon, C. Wong, J. H. Jia, L. L. Wang, Tetrahedron 1986, 42, 655; Y.-M. Man, T. C. W. Mak, H. N. C. Wong, J. Org. Chem. 1990, 55, 3214.