Facile and Chemoselective Microwave-Assisted Cleavage of Oximes to Their Corresponding Carbonyl Compounds Using N,N′ -Dibromo- N,N′-1,3-propylene- bis[(4-methylphenyl)sulfonamide] as a Deoximating Reagent

Abstract

Aldoximes and ketoximes are converted to the parent carbonyl compounds in good yields when treated with N,N′-dibromo-N,N′-1,3-propylene-bis[(4-methylphenyl)sulfonamide] (2) under microwave irradiation. The simple workup minimizes the loss of product and oximes have been selectively oxidized in the presence of alcohols and alkenes.

Key words

aldoximes - carbonyl compounds - ketoximes - microwave irradiation - selective

References

• 1 Sandler SR. Karo W. Organic Functional Group Preparations   2nd ed., Vol. 3:  Academic Press; San Diego: 1989.  p.431-476  
• 2 Green T. W., Wuts P. G. M.; Protective Groups in Organic Synthesis; Wiley: New York, 1991; 2nd ed., 214
• 3 Donaruma LG. Heldt WZ. Org. React.  1960,  11:  1 
• 4 Olah GA. Liao Q. Lee SC. Surya Perakash GK. Synlett  1993,  427 
• 5 Drabowicz J. Synthesis  1980,  125 
• 6 Donaldson RE. Saddler JC. Boyrn S. Mckenzie AT. Fuchs PL. J. Org. Chem.  1983,  48:  2167 
• 7 Corey EJ. Hopkins PB. Kim S. Kou S. Nambiar KP. Flack JR. J. Am. Chem. Soc.  1979,  1901:  7131 
• 8 Curran DP. Brill JF. Rakiewicz DM. J. Org. Chem.  1984,  49:  1654 
• 9 Barhate NB. Gajare AS. Wakharkar RD. Sudalai A. Tetrahedron Lett.  1997,  38:  653 
• 10 Loupy A. Bram G. Villemin D. Solid Support and Catalysts in Organic Synthesis   Smith K. Ellis-Harwood; Chichester UK: 1992.  Chap. 12. p.302-326  
• 11 Khazaei A. Shirdarreh A. Synth. Commun.  1999,  29:  4079