Convenient, mild catalytic deprotection of oximes to carbonyl compounds with hydrogen peroxide and iodine catalyst in aqueous acetonitrile

Synthetic Communications

Volumn 39, Issue 22, 2009, Pages 4053-4061

  Ganguly, Nemai C ^a   Nayek, Subhasis ^a   Barik, Sujoy Kumar ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

30 hydrogen peroxide; Aldehyde; Iodine; Ketone; Oxime

Indexed keywords

4 AMINO 3 IODOACETOPHENONE OXIME; 4 HYDROXY 3,5 DIIODOACETOPHENONE OXIME; ACETONITRILE; CARBON; CARBONYL DERIVATIVE; HYDROGEN PEROXIDE; IODINE; IODINE DERIVATIVE; IODONIUM ION; NITROGEN; NUCLEOPHILE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY;

EID: 70350655960     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902883678     Document Type: Article

References (21)

1. Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P. The palladium assisted transfer reduction of a,b-unsaturated nitroalkenes to oximes using ammonium formate. Synth. Commun. 1990, 20, 2453-2458
2. Larock, R. C. Comprehensive Organic Transformations; Wiley-VCH: New York, 1999; p. 1227
3. Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. A new photochemical reaction. J. Am. Chem. Soc. 1961, 83, 4076-4083
4. Coma, A.; Serna, P.; Garcia, H. Gold catalyst opens a new general che-moselective route to synthesize oximes by hydrogenation of a,b-unsaturated nitro compounds with H2. J. Am. Chem. Soc. 2007, 129, 6358-6359.
5. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1997; pp. 355-356
6. Corsaro, A.; Chiacchio, U.; Pistara, V. Regeneration of carbonyl compounds from the corresponding oximes. Synthesis 2001, 1903-1934.
7. Chaudhuri, S. S.; Akamanchi, K. G. Deoximation using Dess-Martin periodinane: Regeneration of ketones from ketoximes. Tetrahedron Lett. 1998, 39, 3209-3212
8. Bose, D. S.; Srinivas, P. Oxidative cleavage of oximes with peroxymonosulfate ion. Synth. Commun. 1997,27, 3835-3838
9. (NH4)2S2O8-silica, microwave: Varma, R. S.; Meshram, H. M. Solid-state deoximation with ammonium persulfate-silica gel: regeneration of carbonyl compounds using microwaves. Tetrahedron Lett. 1997, 38, 5427-5428
10. Chloramine T: Gupta, K. P.; Manral, L.; Ganesan, K. An efficient approach for the conversion of oximes into carbonyl compounds using dichloramine-T. Synthesis 2007, 1930-1932.
11. Ph3P, 2,2'-dipyridyl diselenide catalyst: Mart́in, M.; Mart́inez, G.; Urṕi, F.; Vilarrasa, J. Conversion of ketoximes to ketones with trimethylphosphine and 2,2'-dipyridyldiselenide. Tetrahedron Lett. 2004, 45, 5559-5561
12. IBX-b-CD catalyst: Krishnaveni, N. S.; Surendra, K.; Nageshwar, Y. V. D.; Rao, K. R. Deoximation of oximes with 2-iodylbenzoic acid in water in the presence of b-cyclodextrin. Synthesis 2003, 1968-1970.
13. I2, H2O-SDS: Gogai, P.; Hazarika, P.; Konwar, D. Surfactant/I2/water: An efficient system for deprotection of oximes and imines to carbonyls under neutral conditions in water. J. Org. Chem. 2005, 70, 1934-1936.
14. Yang, Y.; Zhang, D.; Wu, L.-Z.; Chen, B.; Zhang, L.-P.; Tung, C.-H. Photosensitized oxidative deprotection of oximes to their corresponding carbonyl compounds by platinum(II) terpyridyl acetylide complex. J. Org. Chem. 2004, 69, 4788-4791
15. Lijser, H. J. P.; Fardoun, F. H.; Sawyer, J. R.; Quant, M. Photosensitized regeneration of carbonyl compounds from oximes. Org. Lett. 2002, 4, 2325-2328.
16. Li, D.; Shi, F.; Guo, S.; Deng, Y. One-pot synthesis of silica gel confined functional liquids: Effective catalyst for deoximation under mild conditions. Tetrahedron Lett. 2004, 45, 265-268.
17. Ganguly, N. C.; Barik, S. K. A facile catalytic method of deoximation with potassium bromide and ammonium molybdate in the presence of hydrogen peroxide in aqueous medium. Synthesis 2008, 425-428 and references cited therein.
18. Zmitek, K.; Zupan, M.; Stavber, S.; Iskra, J. The effect of iodine on the peroxidation of carbonyl compounds. J. Org. Chem. 2007, 72, 6534-6540
19. Jereb, M.; Zupan, M.; Stavber, S. Hydrogen peroxide induced iodine transfer into alkenes. Green Chem. 2005, 7, 100.
20. Cerritelli, S.; Chiarini, M.; Cerichelli, G.; Capone, M.; Marsili, M. Supramo-lecular assemblies as promoters of iodohydrin formation. Eur. J. Org. Chem. 2004, 623-630.
21. Kajigaeshi, S.; Kakinama, T.; Yamasaki, H.; Fujisaki, S.; Kondo, M.; Okamoto, T. Iodination of phenols by use of benzyltrimethylammonium dichloroiodate. Chem. Lett. 1987, 2109-2112.