An unprecedented radical reaction of benzotriazole derivatives. A new efficient method for the generation of iminyl radicals

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1556-1557

  El Kaim, L ^a   Meyer, C ^a  

^a ENSTA PARISTECH   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000107516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952173q     Document Type: Article

References (18)

1. See, for instance: (a) Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1745. (b) Atmaran A.; Forrester A. E.; Gill, M.; Fhomson, R. H. J. Chem. Soc., Perkin Trans. 1 1981, 1721.
2. See, for instance: (a) Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1745. (b) Atmaran A.; Forrester A. E.; Gill, M.; Fhomson, R. H. J. Chem. Soc., Perkin Trans. 1 1981, 1721.
3. Campbell, C. D.; Rees, C. W. J. Chem. Soc. C 1969, 742.
4. Barton, D. H. R.; Blundell, P.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1989, 30, 2341.
5. (a) Rees, C. W.; Storr, R. C. J. Chem. Soc. C 1969, 1474.
6. (b) Pojer, P. M. Aust. J. Chem. 1979, 32, 2787.
7. Aurrecoechea, J. M.; Fernandez-Acebes, A. Tetrehedron Lett. 1993, 34, 549.
8. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
9. (b) Curran, D P. Synthesis 1988, 417, 489.
10. Addition of stannyl radicals to aryl triazenes to form stannylamines and aromatic radicals by loss of nitrogen has been reported but has received no synthetic application in radical chemistry: Hollaender, J.; Neumann, W. P.; Alester G. Chem. Ber. 1972, 105, 1540. Radical addition to azide have been shown to proceed by a radical attack on nitrogen: Kim, S.; Joe G. H.; Do T. Y. J. Am. Chem. Soc. 1994, 116, 5521.
11. Addition of stannyl radicals to aryl triazenes to form stannylamines and aromatic radicals by loss of nitrogen has been reported but has received no synthetic application in radical chemistry: Hollaender, J.; Neumann, W. P.; Alester G. Chem. Ber. 1972, 105, 1540. Radical addition to azide have been shown to proceed by a radical attack on nitrogen: Kim, S.; Joe G. H.; Do T. Y. J. Am. Chem. Soc. 1994, 116, 5521.
12. Barton, D. H. R.; Jaszberenyi, J. Cs.; Theodorakis, E. A. J. Am. Chem. Soc. 1992, 114, 5904.
13. Begtrup, M.; Elguero, J.; Faure, R.; Camps, P.; Estopa, C.; Ilavsky, D.; Fruchier, A.; Marzin, C.; De Mendoza, J. Magn. Reson. Chem. 1988, 26, 134.
14. Katrytzky A. R.; S. Rachwall; G. J. Hitchings. Tetrahedron 1991, 47, 2683-2732.
15. The starting ketones were prepared according to: Lorette, N. B.; Howard, W. L. J. Org. Chem. 1961, 26, 3112 for 1b. Tsuji, N.; Suzuki, J.; Shiota, M.; Takahashi, I.; Nishimura, S. J. Org. Chem. 1980, 45, 2729. Christiansen, R. G. U.S. Patent 3,287,355, 1966; Chem. Abstr. 1967, 66, 38145b for 2a.; Ghosez, L.; Montaigne, R.; Roussel, A.; Vanlierde, H.; Mollet, P. Tetrahedron 1971, 27, 615 for 4b. Reference 1 for 5a and 6a.
16. The starting ketones were prepared according to: Lorette, N. B.; Howard, W. L. J. Org. Chem. 1961, 26, 3112 for 1b. Tsuji, N.; Suzuki, J.; Shiota, M.; Takahashi, I.; Nishimura, S. J. Org. Chem. 1980, 45, 2729. Christiansen, R. G. U.S. Patent 3,287,355, 1966; Chem. Abstr. 1967, 66, 38145b for 2a.; Ghosez, L.; Montaigne, R.; Roussel, A.; Vanlierde, H.; Mollet, P. Tetrahedron 1971, 27, 615 for 4b. Reference 1 for 5a and 6a.
17. The starting ketones were prepared according to: Lorette, N. B.; Howard, W. L. J. Org. Chem. 1961, 26, 3112 for 1b. Tsuji, N.; Suzuki, J.; Shiota, M.; Takahashi, I.; Nishimura, S. J. Org. Chem. 1980, 45, 2729. Christiansen, R. G. U.S. Patent 3,287,355, 1966; Chem. Abstr. 1967, 66, 38145b for 2a.; Ghosez, L.; Montaigne, R.; Roussel, A.; Vanlierde, H.; Mollet, P. Tetrahedron 1971, 27, 615 for 4b. Reference 1 for 5a and 6a.
18. The starting ketones were prepared according to: Lorette, N. B.; Howard, W. L. J. Org. Chem. 1961, 26, 3112 for 1b. Tsuji, N.; Suzuki, J.; Shiota, M.; Takahashi, I.; Nishimura, S. J. Org. Chem. 1980, 45, 2729. Christiansen, R. G. U.S. Patent 3,287,355, 1966; Chem. Abstr. 1967, 66, 38145b for 2a.; Ghosez, L.; Montaigne, R.; Roussel, A.; Vanlierde, H.; Mollet, P. Tetrahedron 1971, 27, 615 for 4b. Reference 1 for 5a and 6a.