The effect of α-alkoxy group in radical-mediated β-fragmentation reactions

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3915-3918

  Kim, Sunggak ^a   Kim, Kwan Hee ^a   Cho, Jin Rai ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXYBENZENE DERIVATIVE; RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0030980975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00778-8     Document Type: Article

References (35)

1. For reviews, see: (a) Curran, D. P. Synthesis 1988, 489.
2. (b) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
3. (c) Dowd, P.; Zhang, W. Chem. Rev. 1993, 93, 2091.
4. For selected examples, see: (a) Ayral-Kaloustian, S.; Agosta, W. C. J. Am. Chem. Soc. 1980, 102, 314.
5. (b) Maeda, Y.; Ingold, K. U. J. Am. Chem. Soc. 1980, 102, 328.
6. (c) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106.
7. (d) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882
8. (e) Crimmins, M. T.; Dudek, C. M.; Cheung, W.-H. Tetrahedron Lett. 1992, 33, 181.
9. (f) Newcomb, M. Tetrahedron 1993, 49, 1151.
10. (a) Keck, G. E.; Yates, J. B. J. Am. Chem. Soc. 1982, 104, 5829.
11. (b) Barton, D. H. R.; Crich, D. Tetrahedron Lett. 1984, 25, 2787.
12. (c) Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5444.
13. (d) Baldwin, J. E.; Adlington, R. M.; Robertson, J. J. Chem. Soc., Chem. Commun. 1988, 1404.
14. (a) Beckwith, A. L. J.; Kazlauskas, R.; Syner-Lyons, M. R. J. Org. Chem. 1983, 48, 4718.
15. (b) Dowd, P.; Choi, S.-C. J. Am. Chem. Soc. 1987, 109, 6548.
16. (c) Suginome, H.; Yamada, S. Tetrahedron 1987, 43, 3371.
17. (d) O'Dell, D. E.; Loper, J. T.; Macdonald, T. L. J. Org. Chem. 1988, 53, 5225.
18. (e) Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565.
19. (f) Murphy, J. A.; Patterson, C. W.; Wooster, N. Tetrahedron Lett. 1988, 29, 955.
20. (g) Walton, W.; Fraser-Reid, B. J. Am. Chem. Soc. 1991, 113, 5791.
21. (h) Rawal, V. H.; Zhong, H. M. Tetrahedron Lett. 1993, 34, 5197.
22. (i) Callier, A-C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 1994, 35, 6109.
23. (a) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron Lett. 1991, 32, 6441.
24. (b) Bowman, W. R.; Clark, D. N.; Marmon, R. J. Tetrahedron, 1994, 50, 1275.
25. (c) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396
26. 3SnH (1.1 equiv)/AIBN (0.1 equiv) by a syringe pump for 3 h to a 0.05M refluxing benzene solution of iodide 6. The remaining reactions were carried out under the similar conditions.
27. (a) Fraser-Reid, B.; Vite, G. D.; Yeung, B.-W. A.; Tsang, R. Tetrahedron Lett. 1988, 29, 1645.
28. (b) Vite, G. D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339.
29. (c) Lopez, J. C.; Alonso, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 6471.
30. (a) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry, p 248, John Wiley & Sons, 1995.
31. (b) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1982, 23, 2505.
32. (c) Bachi, M. D.; Frolow, F.; Hoornaert, C. J. Org. Chem. 1983, 48, 1841.
33. (d) Colombo, L.; Giacomo, M. D.; Scolastico, C.; Manzoni, L.; Belvisi, L.; Moteni, V. Tetrahedron Lett. 1995, 36, 625.
34. (a) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1993, 115, 3328.
35. (b) Kim, S.; Joe, G. H.; Do, J. Y. J. Am. Chem. Soc. 1994, 116, 5521.