Intramolecular Homolytic Substitution Behavior of Acyl Radicals at Sulfur: New Carbonylative Access to γ-Thiolactones

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7550-7551

  Ryu, Ilhyong ^a   Okuda, Tohru ^a   Nagahara, Kiyoto ^a   Kambe, Nobuaki ^a   Komatsu, Mitsuo ^a   Sonoda, Noboru ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001641906     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971682k     Document Type: Article

References (29)

1. For recent reviews on acyl radicals, see: (a) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363. (b) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (c) Crich, D.; Yuan, H. In Advances in Free Radical Chemistry; Rawal, V. H., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, in press.
2. For recent reviews on acyl radicals, see: (a) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363. (b) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (c) Crich, D.; Yuan, H. In Advances in Free Radical Chemistry; Rawal, V. H., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, in press.
3. For recent reviews on acyl radicals, see: (a) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363. (b) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (c) Crich, D.; Yuan, H. In Advances in Free Radical Chemistry; Rawal, V. H., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 2, in press.
4. Also see a review containing C1 radical synthons: (d) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. (Washington, D.C.) 1996, 96, 177.
5. 2E) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) (PhTeTePh, RCOTePh) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
6. 2E) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) (PhTeTePh, RCOTePh) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
7. 2E) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) (PhTeTePh, RCOTePh) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
8. Also see examples of group 17 element (iodine): (d) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (e) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465.
9. Also see examples of group 17 element (iodine): (d) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (e) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465.
10. H2 reactions of alkyl and aryl radicals at group 16 elements, see: (a) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (b) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265. (c) Schiesser, C. H. Main Group Chem. News 1993, 1, 8. (d) Crich, D. In Organosulfur Chemistry; Page, P., Ed.; Academic Press: London, 1995; p 49.
11. H2 reactions of alkyl and aryl radicals at group 16 elements, see: (a) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (b) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265. (c) Schiesser, C. H. Main Group Chem. News 1993, 1, 8. (d) Crich, D. In Organosulfur Chemistry; Page, P., Ed.; Academic Press: London, 1995; p 49.
12. H2 reactions of alkyl and aryl radicals at group 16 elements, see: (a) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (b) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265. (c) Schiesser, C. H. Main Group Chem. News 1993, 1, 8. (d) Crich, D. In Organosulfur Chemistry; Page, P., Ed.; Academic Press: London, 1995; p 49.
13. H2 reactions of alkyl and aryl radicals at group 16 elements, see: (a) Beckwith, A. L. J. Chem. Soc. Rev. 1993, 143. (b) Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265. (c) Schiesser, C. H. Main Group Chem. News 1993, 1, 8. (d) Crich, D. In Organosulfur Chemistry; Page, P., Ed.; Academic Press: London, 1995; p 49.
14. Also see an early review: (e) Kampmeier, J. A.; Jordan, R. B.; Liu, M. S.; Yamanaka, H.; Bishop, D. J. In Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; American Chemical Society: Washington, DC, 1978; p 275. (f) Ingold, K. U.; Roberts, B. P. Free Radical Substitution Reactions; Wiley-Interscience: New York, 1971.
15. Also see an early review: (e) Kampmeier, J. A.; Jordan, R. B.; Liu, M. S.; Yamanaka, H.; Bishop, D. J. In Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; American Chemical Society: Washington, DC, 1978; p 275. (f) Ingold, K. U.; Roberts, B. P. Free Radical Substitution Reactions; Wiley-Interscience: New York, 1971.
16. Wang, M.-D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. Also see a review: Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414.
17. Wang, M.-D.; Calet, S.; Alper, H. J. Org. Chem. 1989, 54, 20. Also see a review: Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414.
18. Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Organometallics 1995, 14, 2672.
19. H2 by a primary alkyt radical, see: Franz, J. A.; Roberts, D. H.; Ferris, K. F. J. Org. Chem. 1987, 52, 2256.
20. 3.
21. (a) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
22. (b) Herbert, N.; Pattenden, G. Synlett 1997, 69.
23. (c) Balogs, A. Ph.D. Thesis, University of Pittsburgh, Pittsburgh, PA, 1996, pp 128-129.
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25. H2 reactions. For recent theoretical studies, see: (a) Smart, B. A.; Schiesser, C. H. J. Chem. Soc., Perkin Trans. 2 1994, 2269. (b) Schiesser, C. H.; Smart, B. A. Tetrahedron 1995, 51, 6051.
26. H2 process by attacking of alkyl radical to sulfur of thioester, see: (a) Tada, M.; Nakamura, T.; Matsumoto, M. J. Am. Chem. Soc. 1988, 110, 4647. (b) Tada, M.; Matsumoto, M.; Nakamura, T. Chem. Lett. 1988, 199.
27. H2 process by attacking of alkyl radical to sulfur of thioester, see: (a) Tada, M.; Nakamura, T.; Matsumoto, M. J. Am. Chem. Soc. 1988, 110, 4647. (b) Tada, M.; Matsumoto, M.; Nakamura, T. Chem. Lett. 1988, 199.
28. (a) Beckwith, A. L. J.; Duggan, S. A. M. J. Chem. Soc., Perkin Trans. 2 1994, 1509.
29. H2 in which aryl radical attacks at sulfur with extrusion of acyl radicals; see: (b) Crich, D.; Yao, Q. J. Org. Chem. 1996, 61, 3566.