Ring strain effects in enyne-allene thermolysis: Switch from the Myers-Saito reaction to the C2-C6 biradical cyclization

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6177-6180

  Schmittel, Michael ^a   Steffen, Jens Peter ^a   Auer, Dominik ^a   Maywald, Michael ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALLENE DERIVATIVE; BENZENE; HETEROCYCLIC COMPOUND;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; HEATING; REACTION ANALYSIS;

EID: 0030762384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01393-2     Document Type: Article

References (25)

1. Thermal and electron transfer induced reactions of enediynes and enyne-allenes, part 11; for part 10 see M. Schmittel, J.-P. Steffen, I. Bohn, Heterocycl. Commun. 1997, in press.
2. M. Schmittel, M. Strittmatter, S. Kiau, Tetrahedron Lett. 1995, 36, 4975.
3. a) M. Schmittel, M. Strittmatter, K. Vollmann, S. Kiau, Tetrahedron Lett. 1996, 37, 999. -
4. b) M. Schmittel, M. Keller, S. Kiau, M. Strittmatter, Chem. Eur. J. 1997, 3, 807.
5. J. G. Garcia, B. Ramos, L. M. Pratt, A. Rodríguez, Tetrahedron Lett. 1995, 36, 7391.
6. T. Gillmann, T. Hulsen, W. Massa, S. Wocadlo, Synlett 1995, 1257.
7. a) R. Nagata, H. Yamanaka, E. Murahashi, I. Saito, Tetrahedron Lett. 1990, 31, 2907. -
8. b) A. G. Myers, E. Y. Kuo, N. S. Finney, J. Am. Chem. Soc. 1989, 111, 8057.
9. For reviews, see: a) M. E. Maier, Synlett 1995, 13. - b) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. - K. K. Wang, Chem. Rev. 1996, 96, 207. - J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
10. For reviews, see: a) M. E. Maier, Synlett 1995, 13. - b) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. - K. K. Wang, Chem. Rev. 1996, 96, 207. - J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
11. For reviews, see: a) M. E. Maier, Synlett 1995, 13. - b) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. - K. K. Wang, Chem. Rev. 1996, 96, 207. - J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
12. For reviews, see: a) M. E. Maier, Synlett 1995, 13. - b) K. C. Nicolaou, W.-M. Dai, Angew. Chem. Int. Ed. Engl. 1991, 30, 1387. - K. K. Wang, Chem. Rev. 1996, 96, 207. - J. W. Grissom, G. U. Gunawardena, D. Klingberg, D. Huang, Tetrahedron 1996, 52, 6453.
13. M. Schmittel, M. Strittmatter, S. Kiau, Angew. Chem. Int. Ed. Engl. 1996, 35, 1843.
14. B. Engels (University of Bonn, Germany), private communication.
15. M. Schmittel, M. Maywald, M. Strittmatter, Synlett 1997, 165.
16. K. C. Nicolaou, P. Maligres, J. Shin, E. de Leon, D. Rideout, J. Am. Chem. Soc. 1990, 112, 7825.
17. Z. Arnold, A. Holý, Collect. Czech. Chem. Commun. 1961, 26, 3059.
18. Diethyldialkynylaluminates were obtained by reacting sodium diethyldihydroaluminate in toluene with the corresponding alkynes: J. H. Ahn, M. J. Joung, N. M. Yoon, J. Org. Chem. 1995, 60, 6173.
19. -1 (C≡C), 1920 (C=C=C).
20. B. Liu, K. K. Wang, J. L. Petersen, J. Org. Chem. 1996, 61, 8503.
21. a) K. Hafner, K. H. Häfner, C. König, M. Kreuder, G. Ploss, G. Schulz, E. Sturm, K. H. Vöpel, Angew. Chem. 1963, 75, 35. -
22. b) M. Neuenschwander, Pure Appl. Chem. 1986, 58, 55.
23. A. Pauli, H. Kolshorn, H. Meier, Chem. Ber. 1987, 120, 1611.
24. Ring strain energies were evaluated from AM1 calculated heats of formation (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902) and strainless heat of formation increments (N. Cohen, S. W. Benson, Chem. Rev. 1993, 93, 2419).
25. Ring strain energies were evaluated from AM1 calculated heats of formation (M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107, 3902) and strainless heat of formation increments (N. Cohen, S. W. Benson, Chem. Rev. 1993, 93, 2419).