Tandem radical reactions: Carbon monoxide addition to alkyl radicals and subsequent acyl radical cyclization onto N,N-diphenylhydrazones

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3580-3581

  Brinza, Irina M ^a   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007148939     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960507l     Document Type: Article

References (48)

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2. For reviews, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417. (c) Curran, D. P. Synthesis 1988, 489. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (e) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995.
3. For reviews, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417. (c) Curran, D. P. Synthesis 1988, 489. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (e) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995.
4. For reviews, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417. (c) Curran, D. P. Synthesis 1988, 489. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (e) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995.
5. For reviews, see: (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: New York, 1986. (b) Curran, D. P. Synthesis 1988, 417. (c) Curran, D. P. Synthesis 1988, 489. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237. (e) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; John Wiley & Sons: New York, 1995.
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14. For related hydrazone studies, see: (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882. (b) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213. (c) Kim, S.; Cho, J. R. Synlett 1992, 629. (c) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (d) Kim, S.; Cheong, J. H.; Yoon, K. S. Tetrahedron Lett. 1995, 36, 6069. (e) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 6069.
15. For related hydrazone studies, see: (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882. (b) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213. (c) Kim, S.; Cho, J. R. Synlett 1992, 629. (c) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (d) Kim, S.; Cheong, J. H.; Yoon, K. S. Tetrahedron Lett. 1995, 36, 6069. (e) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 6069.
16. For related hydrazone studies, see: (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882. (b) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213. (c) Kim, S.; Cho, J. R. Synlett 1992, 629. (c) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (d) Kim, S.; Cheong, J. H.; Yoon, K. S. Tetrahedron Lett. 1995, 36, 6069. (e) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 6069.
17. For related hydrazone studies, see: (a) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882. (b) Kim, S.; Kee, I. S. Tetrahedron Lett. 1993, 34, 4213. (c) Kim, S.; Cho, J. R. Synlett 1992, 629. (c) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (d) Kim, S.; Cheong, J. H.; Yoon, K. S. Tetrahedron Lett. 1995, 36, 6069. (e) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron 1995, 51, 6069.
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19. For leading references, see: (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda, H. J. Chem. Soc., Chem. Commun. 1991, 1018. (c) Tsunoi, S.; Ryu, I.; Sonoda, H. J. Am. Chem. Soc. 1994, 116, 5473. (d) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, H. J. Org. Chem. 1995, 60, 7384. For a recent review see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
20. For leading references, see: (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda, H. J. Chem. Soc., Chem. Commun. 1991, 1018. (c) Tsunoi, S.; Ryu, I.; Sonoda, H. J. Am. Chem. Soc. 1994, 116, 5473. (d) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, H. J. Org. Chem. 1995, 60, 7384. For a recent review see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
21. For leading references, see: (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda, H. J. Chem. Soc., Chem. Commun. 1991, 1018. (c) Tsunoi, S.; Ryu, I.; Sonoda, H. J. Am. Chem. Soc. 1994, 116, 5473. (d) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, H. J. Org. Chem. 1995, 60, 7384. For a recent review see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
22. For leading references, see: (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda, H. J. Chem. Soc., Chem. Commun. 1991, 1018. (c) Tsunoi, S.; Ryu, I.; Sonoda, H. J. Am. Chem. Soc. 1994, 116, 5473. (d) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, H. J. Org. Chem. 1995, 60, 7384. For a recent review see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
23. For leading references, see: (a) Ryu, I.; Kusano, K.; Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1990, 112, 1295. (b) Ryu, I.; Kusano, K.; Hasegawa, M.; Kambe, N.; Sonoda, H. J. Chem. Soc., Chem. Commun. 1991, 1018. (c) Tsunoi, S.; Ryu, I.; Sonoda, H. J. Am. Chem. Soc. 1994, 116, 5473. (d) Nagahara, K.; Ryu, I.; Kambe, N.; Komatsu, M.; Sonoda, H. J. Org. Chem. 1995, 60, 7384. For a recent review see: Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
24. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
25. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
26. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
27. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
28. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
29. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
30. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
31. For leading references on acyl radical reactions, see: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. (c) Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. (d) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (e) Boger, D. L.; Mathvink, R. J. J Org. Chem. 1992, 57, 1429. (f) Betty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. (g) Crich, D.; Chen, C.; Hwang, J.-H.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. (h) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271. (i) Chen, L.; Gill, G. B.; Pattenden, G.; Simonian, H. J. Chem. Soc., Perkin Trans. 1 1996, 31.
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