Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 15
462
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Reductive Deoximation of Aryloximes into Hydrocarbons by Hydrazine/KOH: A Novel Application of the Wolff–Kishner Reduction

&
Pages 2183-2187 | Received 06 Jan 2006, Published online: 16 Feb 2007

References

  • Greene , T. G. and Wuts , P. G. M. 1991 . Protective Groups in Organic Synthesis , 3rd ed. New York : John Wiley & Sons .
  • Rao , C. G. , Radhakrishna , A. S. , Singh , B. P. and Bhatnagar , S. P. 1983 . Oxidative cleavage of oximes with triethylammonium chlorochromate . Synthesis , : 808
  • Kharzae , A. and Manesh , A. A. 2005 . Facile regeneration of carbonyl compounds from oximes under microwave irradiation using N‐bromophthalimide . J. Braz. Chem. Soc. , 16 : 874 – 876 .
  • Verma , R. S. and Meshram , H. M. 1997 . Solid state deoximation with ammonium persulfate–silica gel: Regeneration of carbonyl compounds using microwaves . Tetrahedron Lett. , 38 : 5427 – 5428 .
  • Barhate , N. B. , Gajare , A. S. , Wakharkar , R. D. and Sudalai , A. 1997 . Facile regeneration of carbonyl compounds from oximes and tosylhydrazones with TBHP . Tetrahedron Lett. , 38 : 653 – 656 .
  • Curran , D. P. , Brill , J. F. and Rakiewicz , D. M. 1984 . A mild conversion of oximes to ketones . J. Org. Chem. , 49 : 1654 – 1656 .
  • Drabowicz , J. 1980 . Rapid deoximation with pyridinium chlorochromate/hydrogen peroxide system . Synthesis , : 125 – 126 .
  • Corey , E. J. , Hopkins , P. B. , Kim , S. , Nambiar , K. P. and Flack , J. R. 1979 . Total synthesis of erythromycins, 5: Total synthesis of erythronolide . J. Am. Chem. Soc. , 101 : 7131 – 7134 .
  • Donaldson , R. E. , Saddler , J. C. , Boyrn , S. , Mckenzie , A. T. and Fuchs , P. L. 1983 . A triply convergent total synthesis of L‐(–)‐prostaglandin E2 . J. Org. Chem. , 48 : 2167 – 2188 .
  • Corsaro , A. , Chiacchio , U. and Pistara , V. 2001 . Regeneration of carbonyl compounds from the corresponding oximes . Synthesis , : 1903 – 1931 .
  • Barman , D. C. , Gohain , M. , Prajapati , D. and Sandhu , J. S. 2002 . Indium trifluoromethanesulfonate [In(OTf)3]—A new catalyst for Beckmann rearrangement of ketoximes and facile dehydration of aldoximes . Indian J. Chem. , 41B : 154 – 156 .
  • Saikia , P. , Ilias , M. , Prajapati , D. and Sandhu , J. S. 2002 . Iodine‐mediated novel and facile dehydration of aldoximes to nitriles . Indian J. Chem. , 41B : 2109 – 2111 .
  • Boruah , M. and Konwar , D. 2002 . AlCl3 · 6H2O/KI/H2O/CH3CN: A new alternate system for dehydration of oximes and amides in hydrated media . J. Org. Chem. , 68 : 7138 – 7139 .
  • Abhiraj , K. and Channegowda , D. 2003 . Zinc/ammonium formate: A new facile system for the rapid and selective reduction of oximes to amines . J. Chem. Res., Synop. , 6 : 332 – 334 .
  • Pitts , M. R. , Harrison , J. R. and Moody , C. J. 2001 . Indium metal as a reducing agent in organic synthesis . J. Chem. Soc., Perkin Trans. 1 , 9 : 955 – 977 .
  • De , S. K. 2004 . RuCl3‐catalyzed facile conversion of arylalkyl ketoximes to amides . Synth. Commun. , 34 : 3431 – 3434 .
  • Huang‐Minlon . 1963 . A simple modification of the Wolff–Kishner reduction . J. Am. Chem. Soc. , 68 : 4487 – 2488 .
  • Pasha , M. A. and Nanjundaswamy , H. M. 2004 . A novel transformation of oximes into hydrazones by hydrazine hydrate . Synth. Commun. , 34 : 3827 – 3831 .
  • Budavari , S. 2001 . The Merck Index , 13th ed. New Jersey : Merck: White House Station .

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.