Proximate, syn-periplanar, rigid imine(nitrone)/ene-, and diazene(diazeneoxy)/ene systems: Syntheses, homoconjugate reactivity and photochemistry

European Journal of Organic Chemistry

Volumn , Issue 5, 2000, Pages 743-762

  Fischer, Gerhard ^a   Fritz, Hans ^a   Rihs, Grety ^a   Hunkler, Dieter ^a   Exner, Kai ^a   Knothe, Lothar ^a   Prinzbach, Horst ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Chromophores; Diazenes; Heterocycles; Imines; Photochemistry

Indexed keywords

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 0034007172     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200003)2000:5<743::AID-EJOC743>3.0.CO;2-I     Document Type: Article

References (162)

1. K. Exner, H. Prinzbach, Chem. Commun. 1998, 749-750.
2. CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W.M. Horspool, P.S. Song), CRC-Press, Boca Raton, 1994. - G. Kaupp, Photochemie I, Houben-Weyl, 5a, Thieme, Stuttgart 1975, p. 278-412. - P. Margaretha in Houben-Weyl, E17e, Thieme, Stuttgart, 1997, p. 109-114, and cit. ref.
3. CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W.M. Horspool, P.S. Song), CRC-Press, Boca Raton, 1994. - G. Kaupp, Photochemie I, Houben-Weyl, 5a, Thieme, Stuttgart 1975, p. 278-412. - P. Margaretha in Houben-Weyl, E17e, Thieme, Stuttgart, 1997, p. 109-114, and cit. ref.
4. CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W.M. Horspool, P.S. Song), CRC-Press, Boca Raton, 1994. - G. Kaupp, Photochemie I, Houben-Weyl, 5a, Thieme, Stuttgart 1975, p. 278-412. - P. Margaretha in Houben-Weyl, E17e, Thieme, Stuttgart, 1997, p. 109-114, and cit. ref.
5. M. Klessinger, J. Michl, Lichtabsorption und Photochemie Organischer Moleküle, VCH, Weinheim, 1989. - N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito. CA, 1991. - G. von Bünau, Th. Wolff, Photochemie - Grundlagen, Methoden, Anwendungen, VCH, Weinheim, 1987, Chapter 4.3.3, p. 120-128. - cf. E. Osawa, O. Yonemitsu, Carbocyctic Cage Compounds, VCH Publishers, New York, 1992, p. 237-239.
6. M. Klessinger, J. Michl, Lichtabsorption und Photochemie Organischer Moleküle, VCH, Weinheim, 1989. - N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito. CA, 1991. - G. von Bünau, Th. Wolff, Photochemie - Grundlagen, Methoden, Anwendungen, VCH, Weinheim, 1987, Chapter 4.3.3, p. 120-128. - cf. E. Osawa, O. Yonemitsu, Carbocyctic Cage Compounds, VCH Publishers, New York, 1992, p. 237-239.
7. M. Klessinger, J. Michl, Lichtabsorption und Photochemie Organischer Moleküle, VCH, Weinheim, 1989. - N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito. CA, 1991. - G. von Bünau, Th. Wolff, Photochemie -Grundlagen, Methoden, Anwendungen, VCH, Weinheim, 1987, Chapter 4.3.3, p. 120-128. - cf. E. Osawa, O. Yonemitsu, Carbocyctic Cage Compounds, VCH Publishers, New York, 1992, p. 237-239.
8. M. Klessinger, J. Michl, Lichtabsorption und Photochemie Organischer Moleküle, VCH, Weinheim, 1989. - N. J. Turro, Modern Molecular Photochemistry, University Science Books, Sausalito. CA, 1991. - G. von Bünau, Th. Wolff, Photochemie - Grundlagen, Methoden, Anwendungen, VCH, Weinheim, 1987, Chapter 4.3.3, p. 120-128. - cf. E. Osawa, O. Yonemitsu, Carbocyctic Cage Compounds, VCH Publishers, New York, 1992, p. 237-239.
9. K. Exner, G. Fischer, N. Bahr, E. Beckmann, M. Lugan, F. Yang, G. Rihs, M. Keller, D. Hunkler, L. Knothe, H. Prinzbach, Eur. J. Org. Chem. 2000, 763-785, following paper.
10. K. Exner, G. Fischer, M. Lugan, H. Fritz, D. Hunkler, M. Keller, L. Knothe, H. Prinzbach, Eur. J. Org. Chem. 2000, 787-806.
11. G. Fischer, Dissertation, University of Freiburg, 1987.
12. [7a] G. Fischer, D. Hunkler, H. Prinzbach, G. Rihs, H. Fritz, Tetrahedron Lett. 1984, 25, 2459-2462. -
13. [7b] G. Fischer, H. Fritz, H. Prinzbach, Tetrahedron Lett. 1986, 27, 1269-1272. -
14. [7c] Cf. W. Marterer, H. Prinzbach, G. Rihs, J. Wirz, J. Lecoultre, E. Heilbronner, Helv. Chim. Acta 1988, 71, 1937-1965. -
15. [7d] For a N=N/C=C/N=N sytem s. K.-H. Lehr, D. Hunkler, E. Hädicke, H. Prinzbach, Chem. Ber. 1982, 115, 1857-1874.
16. [8a] M. J. Goldstein, R. Hoffmann, J. Am. Chem. Soc: 1971, 93, 6193-6204. -
17. [8b] G. Sedelmeier, H. Prinzbach, H.-D. Martin, Helv. Chimia Acta, 1979, 33, 329-332. -
18. [8c] H.-D. Martin, B. Mayer, Angew. Chem. 1983, 95, 281-313; Angew. Chem. Int. Ed. Engl. 1983, 22, 283. -
19. [8c] H.-D. Martin, B. Mayer, Angew. Chem. 1983, 95, 281-313; Angew. Chem. Int. Ed. Engl. 1983, 22, 283. -
20. [8d] R. Gleiter, R. Schäfer, Acc. Chem. Res. 1990, 23, 369-375.
21. H.-D. Martin, R. Schwesinger, Chem. Ber. 1974, 107, 3143-3145. - B.A.R.C. Murty, P.R. Spun, R. Pinkos, C. Grund, W.-D. Fessner, D. Hunkler, H. Fritz, W. R. Roth, H. Prinzbach, Chimia 1987, 41, 32-36, and cited ref. - J. P. Melder, F. Wahl, H. Fritz, H. Prinzbach, Chimia 1987, 41, 426-428, and cited ref.
22. H.-D. Martin, R. Schwesinger, Chem. Ber. 1974, 107, 3143-3145. - B.A.R.C. Murty, P.R. Spun, R. Pinkos, C. Grund, W.-D. Fessner, D. Hunkler, H. Fritz, W. R. Roth, H. Prinzbach, Chimia 1987, 41, 32-36, and cited ref. - J. P. Melder, F. Wahl, H. Fritz, H. Prinzbach, Chimia 1987, 41, 426-428, and cited ref.
23. H.-D. Martin, R. Schwesinger, Chem. Ber. 1974, 107, 3143-3145. - B.A.R.C. Murty, P.R. Spun, R. Pinkos, C. Grund, W.-D. Fessner, D. Hunkler, H. Fritz, W. R. Roth, H. Prinzbach, Chimia 1987, 41, 32-36, and cited ref. - J. P. Melder, F. Wahl, H. Fritz, H. Prinzbach, Chimia 1987, 41, 426-428, and cited ref.
24. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
25. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. -T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
26. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
27. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
28. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
29. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
30. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
31. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
32. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
33. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
34. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
35. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
36. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
37. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
38. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
39. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
40. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
41. T. J. Chow, Y.-S. Chao, Synth. Comm. 1988, 18, 1875-1881. - T.-C Chou, K.-S. Chuang, C.-T. Lin, J. Org. Chem. 1988, 53, 5168-5170. - J. Behr, R. Braun, H.-D. Martin, M. B. Rubin, A. Steisel, Chem. Ber. 1991, 124, 815-820. - W.-D. Fessner, K. Scheumann, H. Prinzbach, Tetrahedron Lett. 1991, 32, 5939-5942. - T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, Tetrahedron Lett. 1994, 35, 4165-4168. - H. Takeshita, H. Kawakane, Y. Ikeda, A. Mori, J. Org. Chem. 1994, 59, 490-492. - W. Grimme, K. Pohl, J. Wortmann, D. Frowein, Liebigs Ann. 1996, 1905-1916. - C.T. Lin, N.-J. Wang, H.-Z. Tseng, T.-C. Chou, J. Org. Chem. 1997, 62, 4857-4861. - W. Grimme, J. Gossel, J. Lex, Angew. Chem. 1998, 110, 479-481; Angew. Chem. Int. Ed. Engl. 1998, 37, 473-475. - W. Grimme, J. Wortmann, D. Frowein, J. Lex, G. Chen, R. Gleiter, J. Chem. Soc., Perkin Trans. 1 1998, 1893-1900; T.-C. Chou, T.-S. Jiang, J.-T. Hwang, C.-T. Lin, K.-J Lin, J. Org. Chem. 1999, 64, 4874-4883. - For recent studies with benzo-anellated derivatives: S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, K. Imada, M. Kuniyoshi J. Org. Chem. 1987, 52, 2653-2656. - W. Grimme, H. T. Kämmerling, J. Lex, R. Gleiter, J. Heinze, M. Dieterich, W. R. Roth, Angew. Chem. 1991, 103, 215-217; Angew. Chem. Int. Ed Engl. 1991, 30, 205-207. - S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68. - Y. Sakamoto, T. Kumazai, K. Matonara, C. Lim, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 919-922. C. Lim, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 1999, 40, 6781-6784.
42. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
43. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
44. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
45. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
46. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
47. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
48. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
49. T. Fukunaga, R. A. Clement, J. Org. Chem. 1977, 42, 270-274. - G. Sedelmeier, W.-D. Fessner, R. Pinkos, C. Grund, B.A.R.C. Murty, D. Hunkler, G. Rihs, H. Fritz, C. Krüger, H. Prinzbach, Chem. Ber. 1986, 119, 3442-3472. - G. Mehta, M. S. Nair, J. Am. Chem. Soc. 1985, 107, 7519-7524. - G. Mehta, J. Chem. Ed. 1982, 59, 313-316. - G. Mehta, K. R. Reddy, J. Org. Chem. 1987, 52, 460-462. - A. Srikrishna, Synth. Comm. 1990, 20, 279-284. - L. A. Paquette, G. A. O'Doherty, J. Am. Chem. Soc. 1991, 113, 7761-7762. - D. Hochstrate, F.-G. Klärner, Liebigs Ann. 1995, 745-754.
50. Parent A″-diene (m = n = 1) and its diketone became the starting materials for the construction of the iso[1.1.1.1]/[2.2.1.1]pagodanes: G. Gescheidt, R. Herges, H. Neumann, J. Heinze, M. Wollenweber, M. Etzkorn, H. Prinzbach, Angew. Chem. 1995, 107, 1109-1112; Angew. Chem. Int. Ed. Engl. 1995, 34, 1016-1019; A. D. Trifunac, D. W. Werst, R. Herges, H. Neumann, H. Prinzbach, M. Etzkorn, J. Am. Chem. Soc. 1996, 118, 9444-9445.
51. Parent A″-diene (m = n = 1) and its diketone became the starting materials for the construction of the iso[1.1.1.1]/[2.2.1.1]pagodanes: G. Gescheidt, R. Herges, H. Neumann, J. Heinze, M. Wollenweber, M. Etzkorn, H. Prinzbach, Angew. Chem. 1995, 107, 1109-1112; Angew. Chem. Int. Ed. Engl. 1995, 34, 1016-1019; A. D. Trifunac, D. W. Werst, R. Herges, H. Neumann, H. Prinzbach, M. Etzkorn, J. Am. Chem. Soc. 1996, 118, 9444-9445.
52. Parent A″-diene (m = n = 1) and its diketone became the starting materials for the construction of the iso[1.1.1.1]/[2.2.1.1]pagodanes: G. Gescheidt, R. Herges, H. Neumann, J. Heinze, M. Wollenweber, M. Etzkorn, H. Prinzbach, Angew. Chem. 1995, 107, 1109-1112; Angew. Chem. Int. Ed. Engl. 1995, 34, 1016-1019; A. D. Trifunac, D. W. Werst, R. Herges, H. Neumann, H. Prinzbach, M. Etzkorn, J. Am. Chem. Soc. 1996, 118, 9444-9445.
53. W. Berning, S. Hünig, Angew. Chem. 1977, 89, 825-826; Angew. Chem. Int. Ed. Engl. 1977, 16, 111; cf. L. A. Paquette, R. Carr, P. Charumiland, J. F. Blount, J. Org. Chem. 1980, 45, 4922-4926. - S. F. Nelsen, M. R. Willi, J. Org. Chem. 1984, 49, 1-6.
54. W. Berning, S. Hünig, Angew. Chem. 1977, 89, 825-826; Angew. Chem. Int. Ed. Engl. 1977, 16, 111; cf. L. A. Paquette, R. Carr, P. Charumiland, J. F. Blount, J. Org. Chem. 1980, 45, 4922-4926. - S. F. Nelsen, M. R. Willi, J. Org. Chem. 1984, 49, 1-6.
55. W. Berning, S. Hünig, Angew. Chem. 1977, 89, 825-826; Angew. Chem. Int. Ed. Engl. 1977, 16, 111; cf. L. A. Paquette, R. Carr, P. Charumiland, J. F. Blount, J. Org. Chem. 1980, 45, 4922-4926. - S. F. Nelsen, M. R. Willi, J. Org. Chem. 1984, 49, 1-6.
56. W. Berning, S. Hünig, Angew. Chem. 1977, 89, 825-826; Angew. Chem. Int. Ed. Engl. 1977, 16, 111; cf. L. A. Paquette, R. Carr, P. Charumiland, J. F. Blount, J. Org. Chem. 1980, 45, 4922-4926. - S. F. Nelsen, M. R. Willi, J. Org. Chem. 1984, 49, 1-6.
57. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
58. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
59. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
60. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
61. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
62. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
63. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
64. K. Beck, S. Hünig, G. Kleefeld, H.-D. Martin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553. - B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475. - H.-D Martin, B. Mayer, K. Peters, S. Hünig, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 120, 195-201. - K. Beck, S. Hünig, Chem. Ber. 1987, 720, 477-483. - S. Hünig, P. Kraft, Heterocydes 1995, 40, 639-652. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwanger-Perl, K. Peters, H. G. von Schnering, Liebigs Ann. 1995, 351-156. - S. Hünig, M. Schmitt, Liebigs Ann. 1995, 1801-1805. - S. Hünig, U. Brand, K. Peters, H. G. von Schnering, Liebigs Ann. 1997, 785-789.
65. [15a] Quantum yields: W. Adam, F. Mazenod, J. Am. Chem. Soc. 1980, 102, 7131-7132. - For DBO, quantum yields up to 0.03 after nπ* excitation have been reported: P. S. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114. - W. D. Clark, C. J. Steel, J. Am. Chem. Soc. 1971, 93, 6347-6355.
66. [15a] Quantum yields: W. Adam, F. Mazenod, J. Am. Chem. Soc. 1980, 102, 7131-7132. - For DBO, quantum yields up to 0.03 after nπ* excitation have been reported: P. S. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114. - W. D. Clark, C. J. Steel, J. Am. Chem. Soc. 1971, 93, 6347-6355.
67. [15a] Quantum yields: W. Adam, F. Mazenod, J. Am. Chem. Soc. 1980, 102, 7131-7132. - For DBO, quantum yields up to 0.03 after nπ* excitation have been reported: P. S. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114. - W. D. Clark, C. J. Steel, J. Am. Chem. Soc. 1971, 93, 6347-6355.
68. [15b] UV absorptions for DBH, DBO: M. J. Mirbach, K.-C. Liu, M. F. Mirbach, W. R. Cherry, N. J. Turro, P. S. Engel, J. Am. Chem. Soc. 1978, 100, 5122-5129. -
69. [15c] For DBH(DBO) oxides: K. Exner, Disseration, University of Freiburg, 1998. -
70. [15d] IR frequencies for DBH(DBO): R. J. Boyd, J. C. Bünzli, J. P. Snyder, M. L. Heyman, J. Am. Chem. Soc. 1973, 95, 6478-6480; for DBH(DBO) oxides). -
71. [15e] NMR data. -
72. [15f] PE data for DBH, DBO: R. J. Boyd, J.-C. Bünzli, J. P. Snyder, J. Am. Chem. Soc. 1976, 98, 2398-2398; for DBH(DBO) monoxide. -
73. [15g] For DBO dioxide: J.-C. Bünzli, H. Olsen, J. P. Snyder, J. Org. Chem. 1977, 42, 614-616. Cf. Table 1 in W. M. Nau, W. Adam, J. C. Scaiano, J. Am. Chem. Soc. 1996, 118, 2742-2743.
74. [15g] For DBO dioxide: J.-C. Bünzli, H. Olsen, J. P. Snyder, J. Org. Chem. 1977, 42, 614-616. Cf. Table 1 in W. M. Nau, W. Adam, J. C. Scaiano, J. Am. Chem. Soc. 1996, 118, 2742-2743.
75. E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145-146; Angew. Chem. Int. Ed. Engl. 1964, 3, 228.
76. E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145-146; Angew. Chem. Int. Ed. Engl. 1964, 3, 228.
77. D. Ginsburg, Propellanes: Structure and Reactions, Verlag Chemie, Weinheim, 1975. - J. Altman, E. Babad, N. Reshef, D. Ginsburg, Tetrahedron 1968, 24, 975-998.
78. D. Ginsburg, Propellanes: Structure and Reactions, Verlag Chemie, Weinheim, 1975. - J. Altman, E. Babad, N. Reshef, D. Ginsburg, Tetrahedron 1968, 24, 975-998.
79. 1/2 (-78 °C) 30 s for the parent 2,3-diazabicyclo[2.2.2]octa-2,5-diene: J. P. Snyder, L. Lee, V.T. Bandurco, C.Y. Yu, R.J. Boyd, J. Am. Chem. Soc. 1972, 94, 3260-3261.
80. S. M. Weinreb, R. R. Staib, Tetrahedron 1982, 38, 3087-3128. - S. M. Weinreb, J. I. Levin, Heterocycles 1979, 12, 949-975. - G. R. Krow, K. J. Henz, S. W. Szczepanski, J. Org. Chem. 1985, 50, 1888-1894, and cit. ref.
81. S. M. Weinreb, R. R. Staib, Tetrahedron 1982, 38, 3087-3128. -S. M. Weinreb, J. I. Levin, Heterocycles 1979, 12, 949-975. - G. R. Krow, K. J. Henz, S. W. Szczepanski, J. Org. Chem. 1985, 50, 1888-1894, and cit. ref.
82. S. M. Weinreb, R. R. Staib, Tetrahedron 1982, 38, 3087-3128. - S. M. Weinreb, J. I. Levin, Heterocycles 1979, 12, 949-975. -G. R. Krow, K. J. Henz, S. W. Szczepanski, J. Org. Chem. 1985, 50, 1888-1894, and cit. ref.
83. M. P. Cava, C. K. Wilkins, Jr., D. R. Dalton, D. Bessho, J. Org. Chem. 1965, 30, 3772-3775.
84. M. Korat, D. Ginsburg, Tetrahedron 1973, 29, 2373-2381.
85. D. I. Schuster, C. W. Kim, J. Org. Chem. 1975, 40, 505-510.
86. R. Schwesinger, Chimia 1985, 39, 269-272. - see also R. Schwesinger, Nachr. Chem. Tech. Lab. 1990, 38, 1214-1226. - R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H. G. v. Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
87. R. Schwesinger, Chimia 1985, 39, 269-272. - see also R. Schwesinger, Nachr. Chem. Tech. Lab. 1990, 38, 1214-1226. - R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H. G. v. Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
88. R. Schwesinger, Chimia 1985, 39, 269-272. - see also R. Schwesinger, Nachr. Chem. Tech. Lab. 1990, 38, 1214-1226. -R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H. G. v. Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
89. H. Kessler, H. Möhrle, G. Zimmermann, J. Org. Chem. 1977, 42, 66-72.
90. See ref. [17], chapter 4.
91. For applications of high-pressure to faciliate the synthesis of bisdiazenes C: K. Exner, D. Hochstrate, M. Keller, F.-G. Klarner, H. Prinzbach, Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. Engl. 1996, 35, 2256-2259. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwager-Perl, K. Peters, H. G. von Schnering, Liebigs Ann., 1995, 351-356.
92. For applications of high-pressure to faciliate the synthesis of bisdiazenes C: K. Exner, D. Hochstrate, M. Keller, F.-G. Klarner, H. Prinzbach, Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. Engl. 1996, 35, 2256-2259. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwager-Perl, K. Peters, H. G. von Schnering, Liebigs Ann., 1995, 351-356.
93. For applications of high-pressure to faciliate the synthesis of bisdiazenes C: K. Exner, D. Hochstrate, M. Keller, F.-G. Klarner, H. Prinzbach, Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. Engl. 1996, 35, 2256-2259. - S. Hünig, P. Kraft, F.-G. Klärner, U. Artschwager-Perl, K. Peters, H. G. von Schnering, Liebigs Ann., 1995, 351-356.
94. For alternative routes see ref. [10] in ref. [7b]
95. The Chemistry of the Carbon-Nitrogen Double Bond in: S. Patai (Ed.) The Chemistry of Functional Groups, Wiley, London-New York - Sydney - Toronto, 1970; G. Tennant, Imines, Nitrones, Nitriles and Isocyanides, in I.O. Sutherland (Ed.) Comprehensive Organic Chemistry, Vol.2, Pergamon Press, Oxford - New York - Toronto - Sydney - Paris - Frankfurt, 1979, part 8, p. 383 and cit. ref.
96. The Chemistry of the Carbon-Nitrogen Double Bond in: S. Patai (Ed.) The Chemistry of Functional Groups, Wiley, London-New York - Sydney - Toronto, 1970; G. Tennant, Imines, Nitrones, Nitriles and Isocyanides, in I.O. Sutherland (Ed.) Comprehensive Organic Chemistry, Vol.2, Pergamon Press, Oxford - New York - Toronto - Sydney - Paris - Frankfurt, 1979, part 8, p. 383 and cit. ref.
97. A. Padwa, Angew. Chem. 1976, 88, 131-144; Angew. Chem. Int. Ed. Engl. 1976, 15, 56-123.
98. A. Padwa, Angew. Chem. 1976, 88, 131-144; Angew. Chem. Int. Ed. Engl. 1976, 15, 56-123.
99. H. Mitsui, S.-J. Zenki, T. Shiota, S.-J. Murahashi, J. Chem. Soc., Chem. Commun. 1984, 874-875.
100. M. Kaftory, I. Amon, J. Am. Chem. Soc. 1984, 106, 7785-7793. - M. Kaftory, J. Am. Chem. Soc. 1983, 105, 3832-3836. - P. Ashkenazi, M. Kaftory, D. Ginsburg, Helv. Chim. Acta 1983, 66, 611-614.
101. M. Kaftory, I. Amon, J. Am. Chem. Soc. 1984, 106, 7785-7793. - M. Kaftory, J. Am. Chem. Soc. 1983, 105, 3832-3836. - P. Ashkenazi, M. Kaftory, D. Ginsburg, Helv. Chim. Acta 1983, 66, 611-614.
102. M. Kaftory, I. Amon, J. Am. Chem. Soc. 1984, 106, 7785-7793. - M. Kaftory, J. Am. Chem. Soc. 1983, 105, 3832-3836. -P. Ashkenazi, M. Kaftory, D. Ginsburg, Helv. Chim. Acta 1983, 66, 611-614.
103. P. Ashkenazi, J. Oliker, D. Ginsburg, Tetrahedron, 1978, 34, 2171-2173.
104. B.T. Gillis, J. Hargaty, J. Org. Chem. 1967, 32, 95-96.
105. H. Olsen, J.P. Snyder, J. Am. Chem. Soc. 1977, 99, 1524-1536.
106. For further such (3+2)cycloadditions s. S. Hünig, M. Schmidt, Liebigs Ann. 1995, 1801-1805.
107. J. P. Snyder, M. L. Heyman, E. N. Suciu, J. Org. Chem. 1975, 40, 1395-1405. - P. Singh, ibid. 1975, 40, 1405-1408.
108. J. P. Snyder, M. L. Heyman, E. N. Suciu, J. Org. Chem. 1975, 40, 1395-1405. - P. Singh, ibid. 1975, 40, 1405-1408.
109. Rev. H. Basch, T. Hoz, Electronic structure of hydrazo, azo and azoxy compounds, chapter 1 in S. Patai, The chemistry of the hydrazo, azo and azoxy groups, Wiley, New York 1997.
110. R. M. Acheson, N. F. Elmore, Adv. Heterocycl. Chem. 1978, 23, 263-482.
111. Prepared following Vogel's recipe: E. Vogel, W. Maier, J. Elmer, Tetrahedron Lett. 1966, 655-658.
112. R. Gleiter, K. Gubernator, W. Grimme, J. Org. Chem. 1981, 46, 1247-1250. - R. Gleiter, H. Zimmermann, W.-D. Fessner, H. Prinzbach, Chem. Ber. 1985, 118, 3856-3860, and cit. ref.
113. R. Gleiter, K. Gubernator, W. Grimme, J. Org. Chem. 1981, 46, 1247-1250. - R. Gleiter, H. Zimmermann, W.-D. Fessner, H. Prinzbach, Chem. Ber. 1985, 118, 3856-3860, and cit. ref.
114. The olefinic protons of the adduct from 1,3-cyclohexadiene and 6 were taken as reference: S. Grabowski, Dissertation, University of Freiburg, 1997.
115. [7b].
116. [7b].
117. Crystallographic data (excluding structure factors) for the structure(s) reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133157 (24). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internal.) + 44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk].
118. E. F. Ullmann, Chem. Ind. (London), 1958, 1173.
119. I.a. R. K. Howe, S. Winstein, J. Org. Chem. 1973, 38, 2797-2801.
120. Cf. G. N. Fickes, Th. E. Metz, J. Org. Chem. 1978, 43, 4057-4061; and cit. ref.; see also G. Jenner, M. Papadopoulos, Tetrahedron Lett. 1982, 23, 4333-4336.
121. Cf. G. N. Fickes, Th. E. Metz, J. Org. Chem. 1978, 43, 4057-4061; and cit. ref.; see also G. Jenner, M. Papadopoulos, Tetrahedron Lett. 1982, 23, 4333-4336.
122. U. Brand, S. Hünig, K. Peters, H. G. von Schnering, Chem. Ber. 1991, 124, 1187-1190. - S. Hünig, U. Brand, K. Peters, F. Prokschy, H. G. von Schnering, Liebigs Ann.l Recueil 1997, 785-789.
123. U. Brand, S. Hünig, K. Peters, H. G. von Schnering, Chem. Ber. 1991, 124, 1187-1190. - S. Hünig, U. Brand, K. Peters, F. Prokschy, H. G. von Schnering, Liebigs Ann./Recueil 1997, 785-789.
124. A. Fehlauer, K.-P. Grosz, M. Solpianka, W. Sucrow, W. J. S. Lockley, W. Lwowski, Chem. Ber. 1976, 109, 253-260.
125. 13C NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart-New York, 1984.
126. G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276. - K. Beck, A. Höhn, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 517-533.
127. G. Fischer, E. Beckmann, H. Prinzbach, G. Rihs, J. Wirz, Tetrahedron Lett. 1986, 27, 1273-1276. - K. Beck, A. Höhn, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 517-533.
128. M. S. Rasch, J. Org. Chem. 1980, 45, 856-867. - R. Sustmann, Tetrahedron Lett. 1971, 2717-2720.
129. M. S. Rasch, J. Org. Chem. 1980, 45, 856-867. - R. Sustmann, Tetrahedron Lett. 1971, 2717-2720.
130. [7a] Ginsburg et al. have published an analogous example, see J. Kettenring, D. Ginsburg, Tetrahedron 1984, 40, 5269-5269.
131. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
132. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
133. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
134. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
135. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
136. A. Padwa, "Photochemistry of the Carbon-Nitrogen Double Bond", Chem. Rev. 1977, 77, 37-68. - A.C. Pratt, "The Photochemistry of Imines", Chem. Soc. Rev. 1977, 6, 63-81. - J. Y. Vanderhoek, P. A. Cerutti, Photochemie II, Houben-Weyl: IV/ 5b, Thieme Verlag, Stuttgart, 1975, 1104-1121 - P. Margaretha, Helv. Chim. Acta 1982, 65, 290-292. - "Essentials of Molecular Photochemistry" (A. Gilbert, J. Baggott), Blackwell Scientif. Pub., London 1991, p. 412. - For a bisimine: E. Tauer, K.-H. Grellmann, A. Heinrich, Liebigs Ann. 1995, 657-660.
137. H. Freytag, Umwandlung tertiärer Amine in Houben-Weyl Methoden der Organischen Chemie, Vol. XI/2., Thieme Verlag, Stuttgart, 1958, p. 200.
138. S. F. Nelsen, J. Org. Chem. 1984, 49, 1-6.
139. rd, revised Ed., Thieme, Stuttgart, 1987, p. 140.
140. N. J. Turro, C. A. Renner, W. H. Waddell, T. J. Katz, J. Am. Chem. Soc. 1976, 98, 4320-4322. - T. J. Katz, S. Acton, J. Am. Chem. Soc. 1973, 95, 2738-39. - B. M. Trost, R.M. Corey, J. Am. Chem. Soc. 1971, 93, 5572-5573.
141. N. J. Turro, C. A. Renner, W. H. Waddell, T. J. Katz, J. Am. Chem. Soc. 1976, 98, 4320-4322. - T. J. Katz, S. Acton, J. Am. Chem. Soc. 1973, 95, 2738-39. - B. M. Trost, R.M. Corey, J. Am. Chem. Soc. 1971, 93, 5572-5573.
142. N. J. Turro, C. A. Renner, W. H. Waddell, T. J. Katz, J. Am. Chem. Soc. 1976, 98, 4320-4322. - T. J. Katz, S. Acton, J. Am. Chem. Soc. 1973, 95, 2738-39. - B. M. Trost, R.M. Corey, J. Am. Chem. Soc. 1971, 93, 5572-5573.
143. [58a] F. D. Greene, S. S. Hecht, J. Org. Chem. 1970, 35, 2482-2486. -
144. [58b] H. Olsen, C. L. Pedersen, Acta Chem. Scand. B 1982, 36, 701-706. -
145. [58c] M. E. Squillacote, A. Bergman, J. De Felippis, E. M. West, Tetrahedron Lett. 1987, 28, 275-278. -
146. [58d] O. Cullmann, M. Vögtle, F. Stelzer, H. Prinzbach, Tetrahedron Lett. 1998, 38, 2303-2306. -
147. [58e] K. Exner, H. Prinzbach, Chem. Commun. 1998, 749-750, and cit. ref.
148. Revs. G. G. Spencer, E. C. Taylor, O. Buchardt, Chem. Rev. 1970, 70, 231. - M. Nastasi, J. Streith, Rearrangements in Ground and Excited States, Vol. 3, Academic Press, New York, 1980, 445. - A. Albini, M. Alpegiani, Chem. Rev. 1984, 84, 43.
149. Revs. G. G. Spencer, E. C. Taylor, O. Buchardt, Chem. Rev. 1970, 70, 231. - M. Nastasi, J. Streith, Rearrangements in Ground and Excited States, Vol. 3, Academic Press, New York, 1980, 445. - A. Albini, M. Alpegiani, Chem. Rev. 1984, 84, 43.
150. Revs. G. G. Spencer, E. C. Taylor, O. Buchardt, Chem. Rev. 1970, 70, 231. - M. Nastasi, J. Streith, Rearrangements in Ground and Excited States, Vol. 3, Academic Press, New York, 1980, 445. - A. Albini, M. Alpegiani, Chem. Rev. 1984, 84, 43.
151. Rev. W. H. Horspool The photochemistry of the hydrazo, azo and azoxy groups, chapter 13 in S. Patai, The chemistry of the hydrazo, azo and azoxy groups, Wiley, New York, 1997.
152. [58b]
153. R. S. Neale, Synthesis 1971, 1-15.
154. H. G. Aurich, W. Weiss, Top. Curr. Chem. 1975, 59, 65-111.
155. P. Singh, E. F. Ullmann, J. Am. Chem. Soc. 1976, 98, 3018-3019. - F. D. Greene, K. Gilbert, J. Org. Chem. 1975, 40, 140-14159. - A. Rassat, P. Rey, J. Chem. Soc., Chem. Commun. 1971, 1161-1162.
156. P. Singh, E. F. Ullmann, J. Am. Chem. Soc. 1976, 98, 3018-3019. - F. D. Greene, K. Gilbert, J. Org. Chem. 1975, 40, 140-14159. - A. Rassat, P. Rey, J. Chem. Soc., Chem. Commun. 1971, 1161-1162.
157. P. Singh, E. F. Ullmann, J. Am. Chem. Soc. 1976, 98, 3018-3019. - F. D. Greene, K. Gilbert, J. Org. Chem. 1975, 40, 140-14159. - A. Rassat, P. Rey, J. Chem. Soc., Chem. Commun. 1971, 1161-1162.
158. V. I. Stenberg, J. E. Schiller, J. Org. Chem. 1970, 35, 2482-2486.
159. Gaussian 94, Revision E.2, 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. B3LYP cf. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652; C. Lee, W. Yane, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
160. Gaussian 94, Revision E.2, 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. B3LYP cf. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652; C. Lee, W. Yane, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
161. Gaussian 94, Revision E.2, 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. B3LYP cf. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652; C. Lee, W. Yane, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
162. B. G. Gowenlock, W. Lüttke, O. Rev. Chem. Soc. 1958. 12, 321.