Novel oxidative nitrogen to carbon rearrangement found in the conversion of anilines to benzaldoximes by treating with HCHO/H2O2

Tetrahedron Letters

Volumn 49, Issue 18, 2008, Pages 2886-2890

  Kapuriya, Naval ^a   Kapuriya, Kalpana ^a   Dodia, Narsinh M ^a   Lin, Yi Wen ^a   Kakadiya, Rajesh ^a   Wu, Chao Ting ^a   Chen, Ching Huang ^a   Naliapara, Yogesh ^b   Su, Tsann Long ^a  

^a INSTITUTE OF BIOMEDICAL SCIENCES   (Taiwan)

^b SAURASHTRA UNIVERSITY   (India)

Author keywords

Amines; Benzaldoximes; Oxidation; Peroxides; Rearrangement

Indexed keywords

4 METHOXYBENZALDOXIME; 4 METHYLBENZALDOXIME; ALKANE DERIVATIVE; ANILINE DERIVATIVE; BENZALDOXIME DERIVATIVE; CARBON; ETHYLENE OXIDE DERIVATIVE; GLYCEROL; HYDROGEN PEROXIDE; N PHENYLOXAZIRANE; NITROGEN; OXIME DERIVATIVE; PARAFORMALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 41349095184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.033     Document Type: Article

References (31)

1. Ballini R., Barboni L., and Filippone P. Chem. Lett. (1997) 475-476
2. Hajipour A.R., Mohammadpoor B.I., and Nikbaghat K.I. Synth. Commun. 29 (1999) 1697-1701
3. Ren R.X., and Ou W. Tetrahedron Lett. 42 (2001) 8445-8446
4. Kuchler L., and Lambert L. Z. Physik. Chem. (Leipzig) B37 (1937) 285
5. Klecka G.M., and Gonsoir S.J. J. Harzard Mater. 13 (1986) 161-168
6. Adams C.D., Scanlan P.A., and Secrist N.D. Environ. Sci. Technol. 28 (1994) 181-1818
7. Maurino V., Calza P., Minero C., Pelizzetti E., and Vincenti M. Chemosphere 35 (1997) 2675-2688
8. Houser J.J., and Sibbio B.A. J. Org. Chem. 42 (1977) 2145-2151
9. Mazzocchi P.H., and Bowen M.W. J. Org. Chem. 40 (1975) 2689-2690
10. Beckett M.A., and Hua I. Environ. Sci. Technol. 34 (2000) 3944-3953
11. Beckett M.A., and Hua I. Water Res. 37 (2003) 2372-2376
12. Stefan M.I., and Bolton J.R. Environ. Sci. Technol. 32 (1998) 1588-1595
13. Clejan L.A., and Cedebaum A.I. Arch. Biochem. Biophys. 298 (1992) 105-113
14. Kukielka E., and Cedebaum A.I. Drug Metab. Dispos. 19 (1991) 1108-1115
15. Clejan L.A., and Cedebaum A.I. Arch. Biochem. Biophys. 285 (1991) 83-89
16. Giumanini A.G., and Verardo G. J. f. Prakt. Chem. 327 (1985) 739-748
17. Giumanini A.G., and Verardo G. J. f. Prakt. Chem. 329 (1987) 1087-1103
18. Hoffman R.V., and Poelker D.J. J. Org. Chem. 44 (1979) 2364-2369
19. Hoffmann R.J., and Kumar A. J. Org. Chem. 50 (1985) 1859-1863
20. Emmons W.D. J. Am. Chem. Soc. 79 (1957) 5739-5754
21. Janowski W.K., Prager R.H., and Smith J.A. J. Chem. Soc., Perkin Trans. 1 19 (2000) 3212-3216
22. Shiozaki M., and Masuko H. Heterocycles 8 (1984) 1727-1728
23. Eibner A. Justus Liebigs Ann. Chem. 302 (1898) 335-370
24. Berrier C., Brahmi R., Carreyre H., Coustard J.M., Jacquesy J.C., and Violeau B. Bull. Soc. Chim. Fr. 5 (1991) 730-737
25. Beckmann E. Chem. Ber. 37 (1904) 3043
26. Brady O.L., and Bennett C.L. J. Chem. Soc. (1927) 894-898
27. Brady L., and Goldstein R.F. J. Chem. Soc. (1926) 1918
28. Owston N.A., Parker A.J., and Williams M.J. Org. Lett. 9 (2007) 73-75
29. Wuyts H., and Koeck H. Bull. Soc. Chim. Belg. 41 (1932) 196-199
30. Shoppee C.W. J. Chem. Soc. (1932) 696-703
31. Hashem S., and Hosseini S.M. Synlett (2001) 99-101