Synthesis and self-aggregation of cyclic alkynes containing helicene

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1097-1099

  Nakamura, Keiichi ^a   Okubo, Hitoshi ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; HELICENES; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; DOSE RESPONSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKYNES; DOSE-RESPONSE RELATIONSHIP, DRUG; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; POLYCYCLIC COMPOUNDS; STEREOISOMERISM;

EID: 0035912342     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015550w     Document Type: Article

References (28)

1. For examples, see: Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans.1 1990, 271. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron: Asymmetry 1996, 7, 109. Also see ref 6.
2. For examples, see: Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans.1 1990, 271. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron: Asymmetry 1996, 7, 109. Also see ref 6.
3. For examples, see: Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans.1 1990, 271. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron: Asymmetry 1996, 7, 109. Also see ref 6.
4. For examples, see: Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans.1 1990, 271. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron: Asymmetry 1996, 7, 109. Also see ref 6.
5. For examples, see: Yamamoto, K.; Ikeda, T.; Kitsuki, T.; Okamoto, Y.; Chikamatsu, H.; Nakazaki, M. J. Chem. Soc., Perkin Trans.1 1990, 271. Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891. Dai, Y.; Katz, T. J.; Nichols, D. A. Angew. Chem., Int. Ed. Engl. 1996, 35, 2109. Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. J. Am. Chem. Soc. 1997, 119, 10054. Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron: Asymmetry 1996, 7, 109. Also see ref 6.
6. Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500. Formation of LB films of the helicene derivative. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166. Okubo, H.; Feng, F.; Nakano, D.; Hirata, T.; Yamaguchi, M.; Miyashita, T. Tetrahedron 1999, 55, 14855. CT complexation of the helicene derivative. Okubo, H.; Nakano, D.; Yamaguchi, M.; Kabuto, C. Chem. Lett. 2000, 1316. Okubo, H.; Nakano, D.; Anzai, S.; Yamaguchi, M. J. Org. Chem. 2001, 66, 557.
7. Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500. Formation of LB films of the helicene derivative. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166. Okubo, H.; Feng, F.; Nakano, D.; Hirata, T.; Yamaguchi, M.; Miyashita, T. Tetrahedron 1999, 55, 14855. CT complexation of the helicene derivative. Okubo, H.; Nakano, D.; Yamaguchi, M.; Kabuto, C. Chem. Lett. 2000, 1316. Okubo, H.; Nakano, D.; Anzai, S.; Yamaguchi, M. J. Org. Chem. 2001, 66, 557.
8. Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500. Formation of LB films of the helicene derivative. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166. Okubo, H.; Feng, F.; Nakano, D.; Hirata, T.; Yamaguchi, M.; Miyashita, T. Tetrahedron 1999, 55, 14855. CT complexation of the helicene derivative. Okubo, H.; Nakano, D.; Yamaguchi, M.; Kabuto, C. Chem. Lett. 2000, 1316. Okubo, H.; Nakano, D.; Anzai, S.; Yamaguchi, M. J. Org. Chem. 2001, 66, 557.
9. Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500. Formation of LB films of the helicene derivative. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166. Okubo, H.; Feng, F.; Nakano, D.; Hirata, T.; Yamaguchi, M.; Miyashita, T. Tetrahedron 1999, 55, 14855. CT complexation of the helicene derivative. Okubo, H.; Nakano, D.; Yamaguchi, M.; Kabuto, C. Chem. Lett. 2000, 1316. Okubo, H.; Nakano, D.; Anzai, S.; Yamaguchi, M. J. Org. Chem. 2001, 66, 557.
10. Okubo, H.; Yamaguchi, M.; Kabuto, C. J. Org. Chem. 1998, 63, 9500. Formation of LB films of the helicene derivative. Feng, F.; Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166. Okubo, H.; Feng, F.; Nakano, D.; Hirata, T.; Yamaguchi, M.; Miyashita, T. Tetrahedron 1999, 55, 14855. CT complexation of the helicene derivative. Okubo, H.; Nakano, D.; Yamaguchi, M.; Kabuto, C. Chem. Lett. 2000, 1316. Okubo, H.; Nakano, D.; Anzai, S.; Yamaguchi, M. J. Org. Chem. 2001, 66, 557.
11. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
12. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
13. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
14. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
15. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
16. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
17. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
18. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
19. For examples, see: Zhang, J.; Pesak, D. J.; Ludwick, J. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4227. McCallien, D. W. J.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 6611. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596. Wu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 297. Kawase, T.; Ueda, N.; Darabi, H. R.; Oda, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1556. Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052. Haley, M. M.; Bell, M. L.; English, J. J.; Johnson, C. A.; Weakley, T. J. R. J. Am. Chem. Soc. 1997, 119, 2956. Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226. Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544.
20. Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019. Also see: Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
21. Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019. Also see: Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
22. Synthesis of a cyclic alkyne containing helicene is reported. Fox, J. M.; Lin, D.; Itagaki, Y.; Fujita, T. J. Org. Chem. 1998, 63, 2031.
23. Polymerization of helicene by aggregation. Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264. Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79.
24. Polymerization of helicene by aggregation. Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264. Nuckolls, C.; Katz, T. J.; Katz, G.; Collings, P. J.; Castellanos, L. J. Am. Chem. Soc. 1999, 121, 79.
25. Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549. Aryl triflates also react rapidly under modified conditions.
26. See Supporting Information.
27. 3) force field. Monte Carlo searches from several different initial conformations yielded the structure shown in Figure 3 as the global minimum. Amber* (McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743). MacroModel Ver 6.0. (Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulsfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440).
28. 3) force field. Monte Carlo searches from several different initial conformations yielded the structure shown in Figure 3 as the global minimum. Amber* (McDonald, D. Q.; Still, W. C. Tetrahedron Lett. 1992, 33, 7743). MacroModel Ver 6.0. (Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulsfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440).