TRANSITION METAL COMPLEXES MEDIATED EFFICIENT AND FACILE CLEAVAGE OF OXIMES AND PHENYLHYDRAZONE TO CARBONYL COMPOUNDS
Abstract
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Graphical Abstract
Purpose: To report a new and efficient method for the regeneration of carbonyl compounds from their oximes and phenylhydrazones by employing
transition metal complexes under mild conditions.
Methods: Different oxime and phenylhydrazone complexes have been examined for this regeneration process and found effective.
Results: A new method for the cleavage of oximes and phenylhydrazone into their corresponding carbonyl compounds has been done successfully.
Conclusion: The present method is of practical significance as it is rapid, high yielding, involves simple work-up under the very mild condition, and it
applicable to both aldehydes and ketones. Thus, it is believed that the present method appears to be viable alternative to existing procedures.
Keywords: Regeneration, Carbonyl compounds, Oximes, Phenylhydrazones, Transition metal complexes.
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References
Greene TW, Wuts PG. Protective Groups in Organic Synthesis. 2nd ed.
New York: John Wiley & Sons; 1991.
Kabala GW, Pace RD, Wadgaonkar PP. The palladium assisted transfer
reduction of a-b-unsaturated nitroalkanes to oximes using ammonium
formate. Synth Commun 1990;20(16):2453-58.
Bose DS, Srinivas P. A mild and versatile method for the oxidative
cleavage of oximes and tosylhydrazones to carbonyl compounds.
Synlett 1998;1998(9):977-8.
Chouwdry SS, Akamanchi KG. A mild, chemoselective, oxidative
method for deoximation using dess–martin periodinane. Synthesis
;1999(5):760-4.
Mukai C, Nomura I, Kataoka O, Hanaoka M. Dicobaltoctacarbonylmediated
deoximation. Synthesis; 1999;11:1872-4.
Sandhyamayee S, Sagarika S, Sabita P, Sukalyan D, Bijay KM.
Deoximation of Keto – and aldoximes to carbonyl compounds. Indian J
Chem 2008;47B(2):259-71.
Arash GC, Shiri L, Javad Z. Efficient Catalytic and Oxidative
Deoximation of Aldoximes and Ketoximes by Ferric Nitrate and Catalytic
Amounts of Bromide Ion. Bull Korean Chem Soc 2008;29:2496.
Das PJ, Das A, Baruah A. Mixed ligand cobalt(II) complex as an
efficient catalyst for oxidative deoximation using hydrogen peroxide.
Indian J Chem B 2010;49B(8):1140-3.
Kamal A, Arifuddin M, Rao MV. Facile and rapid regeneration
of carbonyl compounds from their N, N-Dimethylhydrazones by
employing transition metal complexes. Synlett 2000;0(10):1482-4.
Abdulla SA, Arun Kumar Y, Arifuddin M, Rajanna KC. Mild and
efficient nitration of aromatic compounds mediated by transition metals
complexes. Synth Commun 2011;41(19):2946-51.
Campbell MJ. Transition metal complexes of thiosemicarbazide and
thiosemicarbazones. Coord Chem Rev 1975;15:279-319.
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