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Synthesis 2001(13): 1903-1931
DOI: 10.1055/s-2001-17700
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Regeneration of Carbonyl Compounds from the Corresponding Oximes

Antonino Corsaro*, Ugo Chiacchio, Venerando Pistarà
Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria 6, 95125 Catania, Italy
Fax: +39(95)580138; e-Mail: acorsaro@dipchi.unict.it;
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Received 5 July 2001
Publikationsdatum:
10. August 2004 (online)

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Abstract

There is a continued interest in the development of procedures for the effective regeneration of carbonyl compounds from the corresponding oximes, especially under mild conditions. Oximes are extensively used as preferred derivatives for purification and characterization of carbonyl compounds and they play an important role as protecting and selectively α-activating groups in synthetic organic chemistry. Furthermore, their synthesis from non-carbonyl compounds provides a valid alternative pathway to carbonyl compounds.

  • 1 Introduction

  • 2 Hydrolytic Methods

  • 2.1 Acidic Hydrolysis

  • 2.2 Neutral or Basic Hydrolysis

  • 2.3 Hydrolysis with Salt Catalysts

  • 2.4 Hydrolysis with Sodium Hydrogensulfite

  • 2.5 Exchange Reaction with other Carbonyl Compounds

  • 2.6 Photohydrolysis

  • 3 Oxidative Methods

  • 3.1 Chromium(VI)

  • 3.2 Manganese(VII, IV, III)

  • 3.3 Thallium(III)

  • 3.4 Cerium(IV)

  • 3.5 Lead(IV)

  • 3.6 Uranium(VI)

  • 3.7 Iron(VI)

  • 3.8 Boron(V)

  • 3.9 Silver(I)

  • 3.10 Cobalt(III)

  • 3.11 Bismuth(V)

  • 3.12 Halogens and Halogenated Compounds

  • 3.13 Peroxidic Compounds

  • 3.14 Ozone

  • 3.15 Oxosulfates

  • 3.16 Nitrosating Agents

  • 3.17 Benzeneseleninic Anhydride

  • 3.18 Electrochemical Oxidative Hydrolysis

  • 4 Reductive Methods

  • 5 Enzymatic Methods

  • 6 Regeneration under Microwave Irradiation

  • 7 Conclusions

Key words

oximes - hydrolysis - oxidation - reduction