Cyclization or hydrogen migration: Theoretical study and experimental evidence on the reactivities of unsaturated amidyl radicals

Organic Letters

Volumn 7, Issue 8, 2005, Pages 1625-1627

  Chen, Qian ^a   Shen, Meihua ^a   Tang, Yu ^a   Li, Chaozhong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMIDE; HYDROGEN;

ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; ENERGY; MATHEMATICAL ANALYSIS; REACTION ANALYSIS; SUBSTITUTION REACTION; THEORETICAL STUDY;

EID: 17844372708     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050437h     Document Type: Article

References (27)

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13. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
14. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
15. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
16. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
17. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
18. For recent examples, see: (a) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539. (b) Hartung, J.; Kneuer, R.; Rummey, C.; Bringmann, G. J. Am. Chem. Soc. 2004, 126, 12121. (c) Shanks, D.; Berlin, S.; Besev, M.; Ottosson, H.; Engman, L. J. Org. Chem. 2004, 69, 1487. (d) Small, D.; Zaitsev, V.; Jung, Y.; Rosokha, S. V.; Head-Gordon, M.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 13850. (e) Zienkiewicz, J.; Kaszynski, P.; Young, V. G., Jr. J. Org. Chem. 2004, 69, 7525. (f) DiLabio, G. A.; Ingold, K. U.; Roydhouse, M. D.; Walton, J. C. Org. Lett. 2004, 6, 4319. (g) Leach, A. G.; Wang, R.; Wohlhieter, G. E.; Khan, S. I.; Jung, M. E.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 4271. (h) Croft, A. K.; Easton, C. J.; Radom, L. J. Am. Chem. Soc. 2003, 125, 4119. (i) Sung, K.; Wang, Y. Y. J. Org. Chem. 2003, 68, 2771. (j) Falzon, C. T.; Ryu, I.; Schiesser, C. H. Chem. Commun. 2002, 2338.
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27. ,6-H migration is a less common process and rare for amidyl radicals in the literature. We also computed such a process for 11 at B3LYP/6-31G* level, which showed a similar trend in activation energy as 1,5-H migration. See the Supporting Information for details.