Nove [3 + 2] radical annulations of cyano-substituted aryl radicals with alkynes

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2441-2442

  Leardini, Rino ^a   Nanni, Daniele ^a   Tundo, Antonio ^a   Zanardi, Giuseppe ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE;

ARTICLE; CYCLIZATION; DIMERIZATION; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 0032537165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00220-2     Document Type: Article

References (24)

1. 1. For free-radicals in synthesis see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon: Oxford, 1986. Curran, D. P. Synthesis 1988, 417 and 489. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic: London, 1992. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996.
2. 1. For free-radicals in synthesis see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon: Oxford, 1986. Curran, D. P. Synthesis 1988, 417 and 489. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic: London, 1992. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996.
3. 1. For free-radicals in synthesis see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon: Oxford, 1986. Curran, D. P. Synthesis 1988, 417 and 489. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic: London, 1992. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996.
4. 1. For free-radicals in synthesis see: Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon: Oxford, 1986. Curran, D. P. Synthesis 1988, 417 and 489. Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis, Academic: London, 1992. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions, VCH: Weinheim, 1996.
5. 2. (a) Albertazzi, A.; Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Org. Chem. 1984, 49, 4482.
6. (b) Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1985, 1390.
7. 3. Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637.
8. 3. Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637.
9. 3. Leardini, R.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1984, 1320. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.; Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Gazz. Chim. Ital. 1989, 119, 637.
10. 4. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1989, 757.
11. 5. Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Synthesis, 1988, 333.
12. 6. (a) Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045.
13. (b) Leardini, R.; Nanni, D.; Pareschi, P.; Tundo, A.; Zanardi, G. J. Org. Chem. 1997, 62, 8394.
14. 7. Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. Tetrahedron 1997, 53, 7929.
15. 7. Beckwith, A. L. J.; O'Shea, D. M.; Westwood, S. W. J. Am. Chem. Soc. 1988, 110, 2565. Montevecchi, P. C.; Navacchia, M. L.; Spagnolo, P. Tetrahedron 1997, 53, 7929.
16. 8. Sakakura, T.; Hara, M.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1985, 1545.
17. 9. Ketone 2 is not stable (see: Wawzonek, S.; Hansen, G. R.; Zigman, A. R. J. Chem. Soc., Chem. Commun. 1969, 6) and has to be recovered by very fast column chromatography.
18. 1H-NMR, MS, and HRMS data. Structure 3b was also confirmed by X-ray diffraction.
19. 11. Iminyl radicals are known to afford dimers. See, for instance: Forrester, A. R.; Gill, M.; Meyer, C. J.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1979, 606.
20. 12. Cyclisations of iminyls onto C-C double bonds: Zard, S. Z. Synlett 1996, 1148 and ref.s cited therein.
21. 13. Homolytic aromatic substitutions by iminyl radicals: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1979, 612. McNab, H.; Smith, G. S. J. Chem. Soc., Perkin Trans. 1 1984, 381. Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1569.
22. 13. Homolytic aromatic substitutions by iminyl radicals: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1979, 612. McNab, H.; Smith, G. S. J. Chem. Soc., Perkin Trans. 1 1984, 381. Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1569.
23. 13. Homolytic aromatic substitutions by iminyl radicals: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1979, 612. McNab, H.; Smith, G. S. J. Chem. Soc., Perkin Trans. 1 1984, 381. Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1569.
24. 13. Homolytic aromatic substitutions by iminyl radicals: Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Perkin Trans. 1 1979, 612. McNab, H.; Smith, G. S. J. Chem. Soc., Perkin Trans. 1 1984, 381. Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1569.