Two novel thermal biradical cyclizations of enyne-ketenimines: Theory, experiment, and synthetic potential

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1562-1564

  Schmittel, Michael ^a   Steffen, Jens Peter ^a   Wencesla Ángel, Miguel Á ^a   Engels, Bernd ^b   Lennartz, Christian ^b   Hanrath, Michael ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Cycloaromatizations; Diradicals; Enynes; Ketenimines; Quantum chemical calculations

Indexed keywords

EID: 0032546774     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1562::AID-ANIE1562>3.0.CO;2-H     Document Type: Article

References (39)

1. M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. 1996, 108, 1952-1954; Angew. Chem. Int. Ed. Engl. 1996, 35, 1843-1845.
2. M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. 1996, 108, 1952-1954; Angew. Chem. Int. Ed. Engl. 1996, 35, 1843-1845.
3. a) A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057-8059;
4. b) R. Nagatab, H. Yamanaka, E. Okazaki, I. Saito, Tetrahedron Lett. 1989, 30, 4995-4998; reviews:
5. c) K. K. Wang, Chem. Rev. 1996, 96, 207-222; J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
6. c) K. K. Wang, Chem. Rev. 1996, 96, 207-222; J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453-6518.
7. M. Schmittel, M. Strittmatter, K. Vollmann, S. Kiau, Tetrahedron Lett. 1996, 37, 999-1002.
8. a) T. Gillmann, T. Hülsen, W. Massa, S. Wocadlo, Synlett 1995, 1257-1259;
9. b) J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodríguez, Tetrahedron Lett. 1995, 36, 7391-7394.
10. M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975-4978.
11. a) M. Schmittel, S. Kiau, Liebigs Ann. Chem. 1997, 733-736;
12. b) M. Schmittel, M. Maywald, M. Strittmatter, Synlett 1997, 165-166;
13. c) M. Schmittel, J.-P. Steffen, I. Bohn, Heterocycl. Commun. 1997, 3, 443-447;
14. d) M. Schmittel, J.-P. Steffen, D. Auer, M. Maywald, Tetrahedron Lett. 1997, 38, 6177-6180;
15. e) Ó. de Frutos, A. M. Echavarren, ibid. 1997, 38, 7941-7942.
16. L. D. Foland, J. O. Karlsson, S. T. Perri, R. Schwabe, S. L. Xu, S. Patil, H. W. Moore, J. Am. Chem. Soc. 1989, 111, 975-989.
17. B. Engels, M. Hanrath, J. Am. Chem. Soc., in press.
18. B. Engels, C. Lennartz, M. Hanrath, M. Schmittel, M. Strittmatter, Angew. Chem., 1998, 110, issue 13/14; Angew. Chem. Int. Ed. 1998, 37, issue 13/14.
19. B. Engels, C. Lennartz, M. Hanrath, M. Schmittel, M. Strittmatter, Angew. Chem., 1998, 110, issue 13/14; Angew. Chem. Int. Ed. 1998, 37, issue 13/14.
20. B. Engels, C. Lennartz, M. Hanrath, unpublished results.
21. A. Szabo, N. S. Ostlund, Modern Quantum Chemistry, Macmillan, New York, 1982.
22. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
23. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
24. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
25. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
26. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
27. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
28. 2 was zero. The calculations were conducted with the Gaussian 94 program package: g) 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, 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, J. A. Pople, Gaussian, Pittsburgh, PA, 1995.
29. [9]
30. a) M. Schmittel, M. Keller, S. Kiau, M. Strittmatter, Chem. Eur. J. 1997, 3, 807-816;
31. b) P. Chen, Angew. Chem. 1996, 108, 1584-1586; Angew. Chem. Int. Ed. Engl. 1996, 35, 1478-1480.
32. b) P. Chen, Angew. Chem. 1996, 108, 1584-1586; Angew. Chem. Int. Ed. Engl. 1996, 35, 1478-1480.
33. Ketenimines can be prepared, for example, by dehydration of amides a) with phosphorous pentoxide in the presence of tertiary amines: C. L. Stevens, G. H. Singhal, J. Org. Chem. 1964, 29, 34-37; b) with triphenylphosphine dibromide and triethylamine: H. J. Bestmann, J. Lienert, L. Mott, Justus Liebigs Ann. Chem. 1968, 718, 24-32: or c) by Staudinger-Wittig reaction of isocyanates with allylidene phosphoranes: L. Capuano, A. Willmes, Justus Liebigs Ann. Chem. 1982, 80-86.
34. Ketenimines can be prepared, for example, by dehydration of amides a) with phosphorous pentoxide in the presence of tertiary amines: C. L. Stevens, G. H. Singhal, J. Org. Chem. 1964, 29, 34-37; b) with triphenylphosphine dibromide and triethylamine: H. J. Bestmann, J. Lienert, L. Mott, Justus Liebigs Ann. Chem. 1968, 718, 24-32: or c) by Staudinger-Wittig reaction of isocyanates with allylidene phosphoranes: L. Capuano, A. Willmes, Justus Liebigs Ann. Chem. 1982, 80-86.
35. Ketenimines can be prepared, for example, by dehydration of amides a) with phosphorous pentoxide in the presence of tertiary amines: C. L. Stevens, G. H. Singhal, J. Org. Chem. 1964, 29, 34-37; b) with triphenylphosphine dibromide and triethylamine: H. J. Bestmann, J. Lienert, L. Mott, Justus Liebigs Ann. Chem. 1968, 718, 24-32: or c) by Staudinger-Wittig reaction of isocyanates with allylidene phosphoranes: L. Capuano, A. Willmes, Justus Liebigs Ann. Chem. 1982, 80-86.
36. E. Differding, L. Ghosez, Tetrahedron Lett. 1985, 26, 1647-1650.
37. -1 (s).
38. R. Bruckner, R. Huisgen, J. Schmid, Tetrahedron Lett. 1990, 31, 7129-7132.
39. A. G. Myers, P. S. Dragovich, E. Y. Kuo, J. Am. Chem. Soc. 1992, 114, 9369-9386.