Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 23
160
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

VO(acac)2 Catalyzed Oxidative Deprotection of Oximes, Hydrazones, and Semicarbazones

Pages 4409-4415 | Received 30 Jul 2004, Published online: 12 Jan 2011

References

  • Greene , T. W. and Wuts , P. G.M. 1999 . “ Protection for the carbonyl group ” . In Protective Groups in Organic Synthesis , 3rd Ed. 352 – 358 . New York : Wiley .
  • Barton , D. H.R. and Beaton , J. M. 1961 . A New Photochemical Reaction . J. Am. Chem. Soc. , 83 : 4076 – 4083 .
  • Hersberg , E. B. 1948 . Regeneration of Steroid Ketones from Their Semicarbazones with Pyruvic Acid . J. Org. Chem. , 13 : 542 – 546 .
  • Bose , S. D. and Narsasiah , A. V. 1999 . Synth. Commun. , 29 : 937
  • Bose , S. D. and Srinivas , P. 1998 . A Mild and Versatile Method for the Oxidative Cleavage of Oximes And Tosylhydrazones to Carbonyl Compounds . Synlett. , : 977 – 978 .
  • Maloney , J. R. , Lyle , R. E. , Saavedra , J. E. and Lyle , G. G. 1978 . Oxidative Deoximation with Pyridinium Chlorochromate . Synthesis , : 212 – 213 . [CROSSREF]
  • Drabowicz , J. 1980 . Rapid Deoximation with Pyridinium Cholorochromate/Hydrogen Peroxide System . Synthesis , : 125 – 126 . [CROSSREF]
  • Chidambaram , N. , Satyanarayan , K. and Chandrasekhar , S. 1989 . An Efficient and Highly Selective Method of Deoximation of Ketoxime . Synth. Commun. , 19 : 1727 – 1734 .
  • Barahate , N. B. , Gajare , A. S. , Waharkar , R. D. and Sudalai , A. 1997 . Facile Regeneration of Carbonyl Compounds from Oximes and Tosylhydrazones with TBHP . Tetrahedron Lett. , 38 : 653 – 656 . [CROSSREF]
  • Demir , A. S. , Tanyeli , C. and Altinel , E. 1997 . Manganese Triacetate Mediated Regeneration of Carbonyl Compounds from Oximes . Tetrahedron Lett. , 38 : 7267 – 7270 . [CROSSREF]
  • Khazaei , A. and Vaghei , R. G. 2002 . Facile Regeneration of Carbonyl Compounds from Oximes Using poly[4‐vinyl‐N,N‐dichlobenzenesulfonamide] . Tetrahedron Lett. , 43 : 3073 – 3074 . [CROSSREF]
  • Arnold , J. N. , Hayes , P. D. , Kohaus , R. L. and Mohan , R. M. 2003 . Bismuth Compounds in Organic Synthesis Deprotection of Ketoximes Using Bismuth Bromide‐Bismuth Trifalte . Tetrahedron Lett. , 44 : 9173 – 9175 . [CROSSREF]
  • Nattier , B. A. , Eash , K. J. and Mohan , R. M. 2001 . Deprotection of Ketoximes Using Bismuth(III) Nitrate Pentahydrate . Synthesis , : 1010 – 1012 . [CROSSREF]
  • Samajdar , S. , Basu , M. K. , Becker , F. F. and Banik , B. K. 2002 . Bismuth Nitrate‐Mediated Deprotection of Oximes . Synth. Commun. , 32 : 1917 – 1921 . [CROSSREF]
  • Ranu , B. C. and Sarkar , D. C. 1988 . A Simple, Efficient, and Highly Selective Method for the Regeneration of Carbonyl Compounds from Oximes and Semicarbazones . J. Org. Chem. , 53 : 878 – 879 .
  • Varma , R. S. , Dahiya , R. and Saini , R. K. 1997 . Solid State Regeneration of Ketones from Oximes on Wet Silica Supported Sodium Periodate Using Microwaves . Tetrahedron Lett. , 38 : 8819 – 8820 . [CROSSREF]
  • Boruah , A. , Baruah , B. , Prajapati , D. and Sandhu , J. S. 1997 . Regeneration of Carbonyl Compounds from Oximes under Microwave Irradiation . Tetrahedron Lett. , 38 : 4267 – 4268 . [CROSSREF]
  • De , S. K. 2003 . SiBr4/Wet Silica Gel as an Efficient Heterogeneous System for Cleavage of C˭N . Tetrahedron Lett. , 44 : 9055 – 9056 . [CROSSREF]
  • De , S. K. 2004 . Cobalt(II) Chloride Catalyzed Chemoselective Thioacetalization of Aldehydes . Tetrahedron Lett. , 45 : 1035 – 1036 . [CROSSREF]
  • De , S. K. 2004 . Ytrrium Triflate as an Efficient and Useful Catalyst for Chemoselective Protection of Carbonyl Compounds . Tetrahedron Lett. , 45 : 2339 [CROSSREF]
  • Ell , A. H. , Jonsson , S. Y. , Borje , A. , Adolfsson , H. and Backbvall , J. E. 2001 . Vanadyl Acetylacetonate as Peroxide Activator in Osmium‐Catalyzed Dihydroxylation of Olefins by Hydrogen Peroxide . Tetrahedron Lett. , 42 : 2569 – 2571 . [CROSSREF]
  • Lattanzi , A. , Senatore , A. , Massa , A. and Scettri , A. 2003 . Novel Highly Regioselective VO(acac)2/TBHP Mediated Oxidation of o‐Alkenyl Phenols to o‐Hydroxybenzyl Ketones . J. Org. Chem. , 68 : 3691 – 3694 . [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Vogel , A. I. 1975 . A Text Book of Practical Organic Chemistry , 3rd Ed. New York : ELBS Longman .
  • Bp and mp are available from Aldrich Chemical Company

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.