2-cyano-iso-propyl radical addition to alkynes

Tetrahedron

Volumn 53, Issue 23, 1997, Pages 7929-7936

  Montevecchi, Pier Carlo ^a   Navacchia, Maria Luisa ^a   Spagnolo, Piero ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; BENZENE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030983396     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00465-1     Document Type: Article

References (32)

1. 1/2 = 2 h at 80 °C) affords 2-cyano-iso-propyl radicals which lead to C-C and C-N dimerization products (Hammond, G. S.; Wu, C. S.; Trapp, O. D.; Warkentin, J.; Keys, R. T. J. Am. Chem. Soc., 1960, 82, 5394).
2. For a recent review on radical additions to alkynes see: Chatgilialoglu, C.; Ferreri, C. Free Radical Addition involving C-C triple bonds. In "The Chemistry of Triple-bonded Functional Groups"; Patai, S., Ed.; J. Wiley: New York, 1994; Suppl. C2, Vol. 2, Chapter 16.
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14. For our relevant papers see Ref. 3, 11, 16, 17, and 18. See also: Benati, L.; Montevecchi, P. C.; Capella, L; Spagnolo, P. J. Org. Chem., 1994, 59, 3368; Benati, L.; Capella, L; Montevecchi, P. C.; P.Spagnolo J. Org. Chem., 1995, 60, 7941; Montevecchi, P. C.; Navacchia, M. L. Tetrahedron Lett., 1996, 37, 6583.
15. For our relevant papers see Ref. 3, 11, 16, 17, and 18. See also: Benati, L.; Montevecchi, P. C.; Capella, L; Spagnolo, P. J. Org. Chem., 1994, 59, 3368; Benati, L.; Capella, L; Montevecchi, P. C.; P.Spagnolo J. Org. Chem., 1995, 60, 7941; Montevecchi, P. C.; Navacchia, M. L. Tetrahedron Lett., 1996, 37, 6583.
16. For our relevant papers see Ref. 3, 11, 16, 17, and 18. See also: Benati, L.; Montevecchi, P. C.; Capella, L; Spagnolo, P. J. Org. Chem., 1994, 59, 3368; Benati, L.; Capella, L; Montevecchi, P. C.; P.Spagnolo J. Org. Chem., 1995, 60, 7941; Montevecchi, P. C.; Navacchia, M. L. Tetrahedron Lett., 1996, 37, 6583.
17. Benati, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1, 1992, 1659
18. Alkyl and imidoyl radicals have been shown to undergo intramolecular cyclization onto a cyano moiety in a 5-exo mode; see ref. 4 and D. L. J. Clive, P. L. Bealieu, L.. Set J. Org. Chem., 1984, 49, 1313.
19. For a recent review on 4-exo radical cyclizations see: Curran, D. P., Porter, N. A., Giese, B, in "Stereochemistry of Radical Reactions", VCH Publisher, New York, 1996, ch. 2.2.2.
20. For examples of β-lactames forming through 4-exo cyclizations see: Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett., 1991, 32, 2335; Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, K.; Kodama, T.; Sato, T.; Ikeda, M. Synlett 1993, 649; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans 1, 1994, 379.
21. For examples of β-lactames forming through 4-exo cyclizations see: Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett., 1991, 32, 2335; Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, K.; Kodama, T.; Sato, T.; Ikeda, M. Synlett 1993, 649; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans 1, 1994, 379.
22. For examples of β-lactames forming through 4-exo cyclizations see: Fremont, S. L.; Belletire, J. L.; Ho, D. M. Tetrahedron Lett., 1991, 32, 2335; Ishibashi, H.; Kameoka, C.; Yoshikawa, A.; Ueda, K.; Kodama, T.; Sato, T.; Ikeda, M. Synlett 1993, 649; Pattenden, G.; Reynolds, S. J. J. Chem. Soc., Perkin Trans 1, 1994, 379.
23. Spagnolo, P., Tiecco, M. Tetrahedron Lett., 1968, 2313; Baigrie, B. D.; Brennan, J.; Cadogan, J. I. G.; Cook, J.; Sharp, J. T. J. Chem. Soc., Perkin Trans. 1, 1975, 1060.
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25. 1,5-Radical migrations are not very common processes; the previously reported examples are mainly confined to the 1,5-hydrogen migration: see Capella, L; Montevecchi, P. C.; Navacchia, M. L. J. Org. Chem., 1995, 60, 7424 and references cited therein.
26. Benati, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1, 1991, 2103; Benati, L.; Capella, L; Montevecchi, P. C.; P. Spagnolo J. Chem. Soc., Perkin Trans. 1, 1995, 1035.
27. Benati, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1, 1991, 2103; Benati, L.; Capella, L; Montevecchi, P. C.; P. Spagnolo J. Chem. Soc., Perkin Trans. 1, 1995, 1035.
28. Capella, L; Montevecchi, P. C.; Nanni, D. J. Org. Chem., 1994, 59, 2818.
29. α-Electron acceptor-substituted vinyl radicals can delocalize the unpaired electron in the sp-linear configuration. The linear configuration is preferred with α-phenyl (see Ref. 17 and references cited therein) and α-trimethylsuyl substituents (Griller, D.; Cooper, J. W.; Ingold, K. U. J. Am. Chem. Soc., 1975, 97, 4269), while contrasting evidence has been reported for the possible configuration of α-oxycarbonylvinyl radicals (Nelson, G. W.; Symons, M. C. R. J. Chem. Soc., PerkinTrans. 2, 1973, 1405; Korth, H.-G.; Lusztyk, J.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2, 1990, 1997).
30. α-Electron acceptor-substituted vinyl radicals can delocalize the unpaired electron in the sp-linear configuration. The linear configuration is preferred with α-phenyl (see Ref. 17 and references cited therein) and α-trimethylsuyl substituents (Griller, D.; Cooper, J. W.; Ingold, K. U. J. Am. Chem. Soc., 1975, 97, 4269), while contrasting evidence has been reported for the possible configuration of α-oxycarbonylvinyl radicals (Nelson, G. W.; Symons, M. C. R. J. Chem. Soc., PerkinTrans. 2, 1973, 1405; Korth, H.-G.; Lusztyk, J.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2, 1990, 1997).
31. α-Electron acceptor-substituted vinyl radicals can delocalize the unpaired electron in the sp-linear configuration. The linear configuration is preferred with α-phenyl (see Ref. 17 and references cited therein) and α-trimethylsuyl substituents (Griller, D.; Cooper, J. W.; Ingold, K. U. J. Am. Chem. Soc., 1975, 97, 4269), while contrasting evidence has been reported for the possible configuration of α-oxycarbonylvinyl radicals (Nelson, G. W.; Symons, M. C. R. J. Chem. Soc., PerkinTrans. 2, 1973, 1405; Korth, H.-G.; Lusztyk, J.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2, 1990, 1997).
32. Oliver, R.; Walton, D. R. M. Tetrahedron Lett., 1972, 5209.