Cyclization of α-Carbonyl Radicals via Condensation of Electron-deficient Alkenes with t-BuHgI and Ph2S2

Synlett

Volumn 1996, Issue 7, 1996, Pages 699-700

  Russell, Glen A ^a   Li, Chaozhong ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001984725     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5572     Document Type: Article

References (24)

1. For reviews, see: (a) Curran, D. P. Synthesis 1988, 417 and 489. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Snider, B. B. Chem. Rev. 1996, 96, 339.
2. For reviews, see: (a) Curran, D. P. Synthesis 1988, 417 and 489. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Snider, B. B. Chem. Rev. 1996, 96, 339.
3. For reviews, see: (a) Curran, D. P. Synthesis 1988, 417 and 489. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Snider, B. B. Chem. Rev. 1996, 96, 339.
4. For reviews, see: (a) Curran, D. P. Synthesis 1988, 417 and 489. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Snider, B. B. Chem. Rev. 1996, 96, 339.
5. For reviews, see: (a) Curran, D. P. Synthesis 1988, 417 and 489. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (c) Melikyan, G. G. Synthesis 1993, 833. (d) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (e) Snider, B. B. Chem. Rev. 1996, 96, 339.
6. Snider, B. B.; Cole, B. M. J. Org. Chem. 1995, 60, 5376.
7. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
8. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
9. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
10. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
11. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
12. For some examples, see: (a) Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1987, 28, 2477. (b) Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140. (d) Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tomo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985. (e) Barth, F.; O-Yang, C. Tetrahedron Lett. 1990, 31, 1121. (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
13. (a) Russell, G. A. Acc. Chem. Res. 1989, 22, 1.
14. (b) Russell, G. A.; Shi, B. Z.; Kim, B. H.; Jiang, W.; Hu, S.; Baik, W. J. Am. Chem. Soc. 1995, 117, 3952.
15. (c) Russell, G. A.; Chen, P.; Yao, C.-F.; Kim, B. H. J. Am. Chem. Soc. 1995, 117, 5967.
16. (d) Russell, G. A.; Li, C.; Chen, P. J. Am. Chem. Soc. 1995, 117, 3645.
17. (e) Russell, G. A.; Li, C. Tetrahedron Lett. 1996, 37, 2557.
18. 2
19. 2NO- (10%) inhibition method.
20. Curran, D. P.; Kim, D.; Liu, H. T.; Shen, W. J. Am. Chem. Soc. 1988, 110, 5900.
21. Theoretical treatment: Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421.
22. Theoretical treatment: (a) Philip, T.; Cook, R. L.; Malloy, J. B.; Allinger, N. L.; Chang, S.; Yuh, Y. J. Am. Chem. Soc. 1981, 103, 2151. (b) Brown, J. M.; Conn, A. D.; Pilcher, G.; Leitao, M. L. P.; Yang, M.-Y. J. Chem. Soc., Chem. Commun. 1989, 1817.
23. Theoretical treatment: (a) Philip, T.; Cook, R. L.; Malloy, J. B.; Allinger, N. L.; Chang, S.; Yuh, Y. J. Am. Chem. Soc. 1981, 103, 2151. (b) Brown, J. M.; Conn, A. D.; Pilcher, G.; Leitao, M. L. P.; Yang, M.-Y. J. Chem. Soc., Chem. Commun. 1989, 1817.
24. 1H NMR (400 M Hz) based on the starting alkenes with the aid of toluene as the internal standard.