Coupling of Fischer Carbene Complexes with Conjugated Enediynes: Generation of Chromium-Complexed Diradicals via the Moore Cyclization and Subsequent Radical Trapping Reactions

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4562-4563

  Herndon, James W ^a   Wang, Haixia ^b  

^a NEW MEXICO STATE UNIVERSITY   (United States)

^b Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000996219     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980300n     Document Type: Article

References (20)

1. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1065-1113.
2. Herndon, J. W.; Hayford, A. Qrganometallics 1995, 14, 1556-1558.
3. For an additional example of a benzannulation reaction induced through the coupling of enediynes with organometallics, see: Wang, Y.; Finn, M. G. J. Am. Chem. Soc. 1995, 777, 8045-8046.
4. Rahm, A.; Wulff, W. D. J. Am. Chem Soc. 1996, 118, 1807-1808.
5. Enediyne 1 was prepared in two steps from 2-(1-hexyn-1-yl)-1-cyclopentenecarboxaldehyde. Wang, K. K.; Liu, B.; Lu, Y. Tetrahedron Lett. 1995, 36, 3785-3788.
6. Wulff, W. D.; Kaesler, R. W.; Peterson, G. A.; Tang, P.-C. J. Am. Chem. Soc. 1985, 707, 1060-1062.
7. (a) For a recent example, see: Moore, H. W.; Xiong, Y. J. Org. Chem. 1996. 67, 9168-9177.
8. (b) For a review, see: Moore, H. W.; Benjamin, R. Y. Chemtracts, Org, Chem. 1992, 5, 273-313.
9. (a) Nguyen, N.; Chow, K.; Karlsson, J. O.; Moore, H. W. J. Org. Chem. 1986, 51, 419-420.
10. (b) Xu, S. L.; Taing, M.; Moore, H. W. J. Org. Chem. 1991, 56, 6104-6109.
11. (c) Xu, S. L.; Moore, H. W. J. Org. Chem. 1992, 57, 326-328.
12. (d) Xia, H.; Moore, H. W. J. Org. Chem. 1992, 57, 3765-3766.
13. (e) For similar process in enyne-allene cyclizations, see; Wang, K. K. Chem. Rev. 1996, 96, 207-222.
14. For a discussion of 6-endo vs 5-exo ring closure of aryl radicals, see: Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072-4078.
15. The indicated stereochemistry is anticipated on the basis of the stereodirecting effect of the chromium tricarbonyl unit, (a) Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 517-549. (b) Davies, S. G. Chem. Ind. 1986, 506-509.
16. The indicated stereochemistry is anticipated on the basis of the stereodirecting effect of the chromium tricarbonyl unit, (a) Semmelhack, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 517-549. (b) Davies, S. G. Chem. Ind. 1986, 506-509.
17. Aromatization of cyclohexadiene derivatives by chromium(0) compounds has precedent. Turner, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404.
18. 3 complexes has been discussed. Heppert, J. A.; Boyle, T. J.; Takusagawa, F. Organometallics 1989, 8, 461-467.
19. - complexes. Semmelhack, M. F.; Hall, H. T., Jr.; Farina, R.; Yoshifuji, M.; Glark, G.; Bargar, T.; Hirotsu, K.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 3535-3544.
20. Wulff, W. D.; Bax, B. B.; Brandvold, T. A.; Chan, K. S.; Gilbert, A. M.; Hsung, R. P.; Mitchell, M.; Clardy, J. Organometallics 1994, 13, 102-126.