Carbonyl oxide chemistry. 5. Nucleophilic trapping reaction with aldo and keto oximes. Synthesis of hydroperoxynitrones

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8677-8680

  Iesce, M Rosaria ^a   Cermola, Flavio ^a   Guitto, Antonio ^a   Giordano, Federico ^a   Scarpati, Rachele ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000433819     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961375z     Document Type: Article

References (36)

1. Iesce, M. R.; Cermola, F.; Guitto, A.; Scarpati, R.; Graziano, M. L. J. Org. Chem. 1995, 60, 5324.
2. 3
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4. 6
5. Reference 1 and references therein.
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10. Erden, I.; Griffin, A.; Keeffe, J. R.; Brinck-Kohn, V. Tetrahedron Lett. 1993, 793. Cf. also: Ching, T. Y.; Foote, C. S. Tetrahedron Lett. 1975, 3771.
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12. 7b,10
13. Graziano, M. L.; Iesce, M. R.; Cimminiello, G.; Scarpati, R. J. Chem. Soc., Perkin Trans. 1 1989, 241.
14. 12
15. Richardson, W. H. In The Chemistry of Peroxides; Patai, S., Ed.; J. Wiley and Sons: New York, 1983; Chapter 5, p 152.
16. 14
17. Dopp, D.; Dopp, H. In Houben-Weyl; Klamann, D., Hagemann, H., Eds.; Thieme: Stuttgart, 1990; Band E14b/2, p 1379.
18. The hypothesis that the rearrangement occurs through the intermediacy of an undetected oxaziridine is to be ruled out since methyl (Z)-3-[2-(1-hydroperoxycyclohexyl)oxaziridin-3-yl]propenoate, casually obtained by prolonged irradiation of the photooxygenation mixture (see Experimental Section), was a stable compound and under no conditions gave the nitrone 5a.
19. The authors have deposited X-ray data for this structure with the Cambridge Crystallographic Data Center. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, UK.
20. The stereochemistry of the carbon-nitrogen double bond of 7c,d, derived from the asymmetric oximes 4c,d, was not assigned.
21. 8
22. For nitrone applications see among others: Kato, K.; Nakano, M.; Richaado, G. K. Jpn. Patent 06239737, 1994; Chem. Abstr. 1995, 122, 1096k. Krimer, M. Z.;, Styngin, E. P.; Rekhten, M. A.; Grushetskaya, G. N.; Uzhavka, Z. N.; Panasenko, A. A.; Molchanov, O. Yu.; Abelentsev, V. I. Zh. Org. Chim. 1983, 29, 1859. Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1986; Vol. III, p 355.
23. For nitrone applications see among others: Kato, K.; Nakano, M.; Richaado, G. K. Jpn. Patent 06239737, 1994; Chem. Abstr. 1995, 122, 1096k. Krimer, M. Z.;, Styngin, E. P.; Rekhten, M. A.; Grushetskaya, G. N.; Uzhavka, Z. N.; Panasenko, A. A.; Molchanov, O. Yu.; Abelentsev, V. I. Zh. Org. Chim. 1983, 29, 1859. Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1986; Vol. III, p 355.
24. For nitrone applications see among others: Kato, K.; Nakano, M.; Richaado, G. K. Jpn. Patent 06239737, 1994; Chem. Abstr. 1995, 122, 1096k. Krimer, M. Z.;, Styngin, E. P.; Rekhten, M. A.; Grushetskaya, G. N.; Uzhavka, Z. N.; Panasenko, A. A.; Molchanov, O. Yu.; Abelentsev, V. I. Zh. Org. Chim. 1983, 29, 1859. Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1986; Vol. III, p 355.
25. For nitrone applications see among others: Kato, K.; Nakano, M.; Richaado, G. K. Jpn. Patent 06239737, 1994; Chem. Abstr. 1995, 122, 1096k. Krimer, M. Z.;, Styngin, E. P.; Rekhten, M. A.; Grushetskaya, G. N.; Uzhavka, Z. N.; Panasenko, A. A.; Molchanov, O. Yu.; Abelentsev, V. I. Zh. Org. Chim. 1983, 29, 1859. Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1986; Vol. III, p 355.
26. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
27. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
28. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
29. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
30. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
31. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
32. For hydroperoxide applications see among others: Oda, K.; Takei, K. Jpn. Patent 0710709, 1995; Chem. Abstr. 1995, 122, 207776r. Inoi, T. Jpn. Patent 0211501, 1990; Chem. Abstr. 1990, 113, 120874m. Organic Peroxides; Ando, W., Ed.; Wiley: Chichester, 1992. Sheldon, R. A. In The Chemistry of Peroxides; Patai, S., Ed.; Wiley: Chichester, 1983; p 161. Kropf, H.; Torkler, F. In Houben-Weyl; Kropf, H., Ed.; Thieme: Stuttgart, 1990; Band E14b/2; p 39.
33. Freeman, J. P. Chem. Rev. 1983, 83, 241.
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35. 1H NMR).
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