Synthesis of Novel Enyne-Allenes, Their Thermal C2-C6 Cyclization, and the Importance of a Benzofulvene Biradical in the DNA Strand Cleavage

Synlett

Volumn 1997, Issue 2, 1997, Pages 165-166

  Schmittel, Michael ^a   Maywald, Michael ^a   Strittmatter, Marc ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002974462     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-726     Document Type: Article

References (25)

1. Thermal and electron transfer induced reactions of enediynes and enyne-allenes, part 7; for part 6 see Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691.
2. For reviews, see: a) Maier, M. E. Synlett 1995, 13. b) Nicolaou, K. C.; Dai, W. M. Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387.
3. For reviews, see: a) Maier, M. E. Synlett 1995, 13. b) Nicolaou, K. C.; Dai, W. M. Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387.
4. For reviews, see: a) Maier, M. E. Synlett 1995, 13. b) Nicolaou, K. C.; Dai, W. M. Angew. Chem. 1991, 103, 1453; Angew. Chem. Int. Ed. Engl. 1991, 30, 1387.
5. For reviews, see: a) Wang, K. K. Chem. Rev. 1996, 96, 207. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
6. For reviews, see: a) Wang, K. K. Chem. Rev. 1996, 96, 207. b) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453.
7. a) Nagata, R.; Yamanaka, H.; Okazaki, E, Saito, I. Tetrahedron Lett. 1989, 30, 4995.
8. b) Myers, A. G. Tetrahedron Lett. 1987, 28, 4493.
9. The only evidence for systems that do not follow the Myers-Saito cyclization has been reported by Bruckner: Scheuplein, S. W.; Machinek, R.; Suffert, J.; Brückner, R. Tetrahedron Lett. 1993, 34, 6549.
10. a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975.
11. b) Schmittel, M.; Strittmatter, M.; Vollmann, K.; Kiau, S. Tetrahedron Lett. 1996, 37, 999.
12. Schmittel, M.; Strittmatter, M.; Kiau, S. Angew. Chem. 1996. 108, 1952; Angew. Chem. Int. Ed. Engl. 1996, 35, 1843.
13. Schmittel, M.; Strittmatter, M.; Kiau, S. Angew. Chem. 1996. 108, 1952; Angew. Chem. Int. Ed. Engl. 1996, 35, 1843.
14. Bennett, J. E.; Howard, J. A. Chem. Phys. Lett. 1971, 9, 460.
15. a) Garcia, J. G.; Ramos, B.; Pratt, L. M.; Rodríguez, A. Tetrahedron Lett. 1995, 36, 7391.
16. b) Gillmann, T.; Hülsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257.
17. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
18. Nantz, M. H.; Bender, D. M.; Janaki, S. Synthesis 1993, 577.
19. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451; Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103.
20. Ruitenberg, K.; Kleijn, H.; Elsevier, C. J.; Meijer, J.; Vermeer, P. Tetrahedron Lett. 1981, 22, 1451; Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103.
21. Keinan, E.; Bosch, E. J. Org. Chem. 1986, 51, 4006.
22. 4Cl and extraction with n-pentane the products were purified by column chromatography.
23. 3; 250 MHz): δ= 1.06 (t, J = 7.2 Hz, 3H), 1.60-1.80 (m, 4H), 2.70 (dt, J = 7.8 Hz, J = 2.6 Hz, 2H), 3.88 (s, 3H), 7.00 (d, J = 9.2 Hz, 2H), 7.34-7.70 (m, 11H); 1R (neat): v = 2239 (C≡C), 1929 (C=C=C).
24. The structure of the benzofulvenes 3e-g could be unambiguously assigned on the basis of their spectral data by comparison with those of X-ray characterized benzofulvene 3b: Schmittel, M.; Keller, M.: Kiau, S.; Strittmatter, M. Eur. J. Chem. submitted for publication.
25. 3; 250 MHz): δ = 1.06 (t, J = 7.3 Hz, 3H), 1.62 (m, 2H), 1.82(m, 2H), 3.21 (t, J = 7.9 Hz, 2H), 3.71 (s, 3H), 4.08 (s, 2H), 6.44 (m, 1H), 6.90 (d, J = 2.8 Hz, 1H), 7.03 (td, J = 7.9 Hz, J = 1.2Hz, 1H), 7.20 (dd, J = 9.1 Hz, J = 2.8 Hz, 1H), 7.23 (m, 1H), 7.43 (dd, J = 7.9 Hz, J = 2.1 Hz, 2H), 7.53-7.56 (m, 1H), 7.58-7.62 (m, 3H), 8.00 (d, J = 9.1 Hz, 1H).