1H-1,3-Diazepines, 5H-1,3-diazepines, 1,3-diazepinones, and 2,4-diazabicyclo[3.2.0]heptenes

Organic and Biomolecular Chemistry

Volumn 2, Issue 8, 2004, Pages 1227-1238

  Reisinger, Ales ^a   Koch, Rainer ^b   Bernhardt, Paul V ^a   Wentrup, Curt ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; CARBON; CRYSTAL STRUCTURE; DRUG PRODUCTS; HYDROLYSIS; INFRARED SPECTROSCOPY; ISOMERS; PHOTOCHEMICAL REACTIONS; X RAY CRYSTALLOGRAPHY;

NUCLEOPHILLIC TRAPPING; PHOTOCHEMICAL RING CLOSURE; PROTON EXCHANGE; RING EXPANSION;

AROMATIC COMPOUNDS;

EID: 2342614197     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b317099c     Document Type: Article

References (29)

1. (a) A. Reisinger, R. Koch and C. Wentrup, J. Chem. Soc., Perkin Trans. 1, 1998, 2247
2. (b) A. Reisinger and C. Wentrup, Chem. Commun., 1996, 813.
3. A. Reisinger, P. V. Bernhardt and C. Wentrup, Org. Biomol. Chem., 2004, 2, 222.
4. D. J. Le Count, Comprehensive Heterocyclic Chemistry II, A. R. Katritzky. C. W. Rees and E. F. V. Scriven, eds, vol 9, p. 139. Elsevier, New York, 1996.
5. P. S. Zurer, Chem. Eng. News, May 5, 1997; P. Y. S. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru, L. C. Bacheler, J. L. Meek, M. C. Otto, M. R. Rayner, Y. N. Wong, C.-H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe and S. Erickson-Viitanen, Science, 1994, 263, 380; C. N. Hodge, P. Y. S. Lam, C. J. Eyerman, P. K. Jadhav, Y. Ru, C. H. Fernandez, G. V. De Lucca, C.-H. Chang, R. F. Kaltenbach, E. R. Holler, F. Woerner, W. F. Daneker, G. Emmett, J. C. calabrese and P. E. Aldrich, J. Am. Chem. Soc., 1998, 120, 4570; F. Qian, J. E. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, K. Kokka and L. McElwee-White, J. Org. Chem., 2002, 67, 4086 and references therein.
6. P. S. Zurer, Chem. Eng. News, May 5, 1997; P. Y. S. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru, L. C. Bacheler, J. L. Meek, M. C. Otto, M. R. Rayner, Y. N. Wong, C.-H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe and S. Erickson-Viitanen, Science, 1994, 263, 380; C. N. Hodge, P. Y. S. Lam, C. J. Eyerman, P. K. Jadhav, Y. Ru, C. H. Fernandez, G. V. De Lucca, C.-H. Chang, R. F. Kaltenbach, E. R. Holler, F. Woerner, W. F. Daneker, G. Emmett, J. C. calabrese and P. E. Aldrich, J. Am. Chem. Soc., 1998, 120, 4570; F. Qian, J. E. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, K. Kokka and L. McElwee-White, J. Org. Chem., 2002, 67, 4086 and references therein.
7. P. S. Zurer, Chem. Eng. News, May 5, 1997; P. Y. S. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru, L. C. Bacheler, J. L. Meek, M. C. Otto, M. R. Rayner, Y. N. Wong, C.-H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe and S. Erickson-Viitanen, Science, 1994, 263, 380; C. N. Hodge, P. Y. S. Lam, C. J. Eyerman, P. K. Jadhav, Y. Ru, C. H. Fernandez, G. V. De Lucca, C.-H. Chang, R. F. Kaltenbach, E. R. Holler, F. Woerner, W. F. Daneker, G. Emmett, J. C. calabrese and P. E. Aldrich, J. Am. Chem. Soc., 1998, 120, 4570; F. Qian, J. E. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, K. Kokka and L. McElwee-White, J. Org. Chem., 2002, 67, 4086 and references therein.
8. P. S. Zurer, Chem. Eng. News, May 5, 1997; P. Y. S. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru, L. C. Bacheler, J. L. Meek, M. C. Otto, M. R. Rayner, Y. N. Wong, C.-H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe and S. Erickson-Viitanen, Science, 1994, 263, 380; C. N. Hodge, P. Y. S. Lam, C. J. Eyerman, P. K. Jadhav, Y. Ru, C. H. Fernandez, G. V. De Lucca, C.-H. Chang, R. F. Kaltenbach, E. R. Holler, F. Woerner, W. F. Daneker, G. Emmett, J. C. calabrese and P. E. Aldrich, J. Am. Chem. Soc., 1998, 120, 4570; F. Qian, J. E. McCusker, Y. Zhang, A. D. Main, M. Chlebowski, K. Kokka and L. McElwee-White, J. Org. Chem., 2002, 67, 4086 and references therein.
9. (a) R. A. Evans, M. W. Wong and C. Wentrup, J. Am. Chem. Soc., 1996, 118, 4009
10. (b) C. Wentrup and H.-W. Winter, J. Am. Chem. Soc., 1980, 102, 6159.
11. F. A. Bovey, Nuclear magnetic Resonance Spectroscopy, Academic Press, New York, 2nd edn.; 1988; J. Sandström, Dynamic NMR Spectroscopy, Academic Press, New York, 1982.
12. F. A. Bovey, Nuclear magnetic Resonance Spectroscopy, Academic Press, New York, 2nd edn.; 1988; J. Sandström, Dynamic NMR Spectroscopy, Academic Press, New York, 1982.
13. S. Forsén and R. A. Hoffman, J. Chem. Phys., 1963, 39, 2892.
14. A. Reisinger, PhD Thesis, The University of Queensland, 2001.
15. J. C. Teulade, A. Gueiffier, J. P. Chapat, G. Grassy, A. Carpy, A. H'Naifi, B. Perly and J. Couquelet, Chem. Pharm. Bull., 1989, 37, 2293; P. Molina, A. Arques, A. Alias, M. C. Foces-Foces and A. L. Llamas-Saiz, J. Chem. Soc., Chem. Commun., 1992, 424.
16. J. C. Teulade, A. Gueiffier, J. P. Chapat, G. Grassy, A. Carpy, A. H'Naifi, B. Perly and J. Couquelet, Chem. Pharm. Bull., 1989, 37, 2293; P. Molina, A. Arques, A. Alias, M. C. Foces-Foces and A. L. Llamas-Saiz, J. Chem. Soc., Chem. Commun., 1992, 424.
17. J. A. Moore, W. J. Freeman, R. C. Gearhart and H. B. Yokelson, J. Org. Chem., 1978, 43, 787.
18. C. J. Addicott, PhD Thesis, The University of Queensland, 2002.
19. R. Koch, B. Wiedel and C. Wentrup, J. Chem. Soc., Perkin Trans. 2, 1997, 1851.
20. (a) R. A. Odum and B. Schmall, J. Chem. Res. (S), 1997, 276; R. A. Odum and B. Schmall, J. Chem. Res. (M), 1997, 1850
21. (a) R. A. Odum and B. Schmall, J. Chem. Res. (S), 1997, 276; R. A. Odum and B. Schmall, J. Chem. Res. (M), 1997, 1850
22. (b) K. Satake, S. Takami, Y. Tawada and M. Kimura, Chem. Commun., 2001, 1382.
23. W. J. Hehre, L. Radom, P. v. R. Schleyer and J. A. Pople, Ab Initio Molecular Orbital Theory, Wiley, New York, 1986.
24. 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 and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
25. J. A. Pople, A. P. Scott, M. W. Wong and L. Radom, Isr. J. Chem., 1993, 33, 345.
26. A. P. Scott and L. Radom, J. Phys. Chem., 1996, 100, 16502.
27. L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837.
28. G. M. Sheldrick, SHELX97 - Programs for Crystal Structure Analysis (Release 97-2), Institut für Anorganische Chemie der Universität, Tamstrasse 4, D-3400, Göttingen, Germany, 1998.
29. L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.