Effect of temperature on 5-endo- and 4-exo-trig radical cyclizations of N-vinylic α-halo amides

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 75-78

  Ishibashi, Hiroyuki ^a   Higuchi, Masahiro ^a   Ohba, Masashi ^a   Ikeda, Masazumi ^b  

^a KANAZAWA UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZENE; CHLOROACETAMIDE; RADICAL; SOLVENT; TOLUENE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ORGANIC CHEMISTRY; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0031962752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10492-0     Document Type: Article

References (21)

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15. 3) δ 1.81-2.24 (m, 8 H), 3.22 (d, J = 16.3 Hz, 1 H), 3.36 (dd, J = 12.5, 3.6, 1 H), 4.22 (d, J = 16.3 Hz, 1 H), 5.13 (s, 1 H), 7.15-7.49 (m, 10 H).
16. 3SnH and AIBN in boiling toluene, gave a complex mixture of products from which compound 12 was isolated in 16% yield. Formation of 12 from 1c may be a result of the 4-exo cyclization followed by ring-opening of the resulting radical 11. The detailed mechanism is under investigation.
17. Quite recently, the effect of temperature on the 5-exo- and 6-endo-trig radical cyclizations onto vinylsilyl ethers has been reported. See: Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676.
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19. Mondon, A.; Zander, J.; Menz, H.-U. Liebigs Ann. Chem. 1963, 667, 126. Rigby, J.H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975. Rigby, J.H.; Hughes, R.C.; Heeg, M.J. J. Am. Chem. Soc. 1995, 117, 7843. Rigby, J.H.; Mateo, M.E. Tetrahedron 1996, 52, 10569.
20. Mondon, A.; Zander, J.; Menz, H.-U. Liebigs Ann. Chem. 1963, 667, 126. Rigby, J.H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975. Rigby, J.H.; Hughes, R.C.; Heeg, M.J. J. Am. Chem. Soc. 1995, 117, 7843. Rigby, J.H.; Mateo, M.E. Tetrahedron 1996, 52, 10569.
21. Mondon, A.; Zander, J.; Menz, H.-U. Liebigs Ann. Chem. 1963, 667, 126. Rigby, J.H.; Qabar, M. J. Am. Chem. Soc. 1991, 113, 8975. Rigby, J.H.; Hughes, R.C.; Heeg, M.J. J. Am. Chem. Soc. 1995, 117, 7843. Rigby, J.H.; Mateo, M.E. Tetrahedron 1996, 52, 10569.