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Synthesis 2005(18): 3023-3025
DOI: 10.1055/s-2005-916027
DOI: 10.1055/s-2005-916027
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate
Further Information
Received
25 May 2005
Publication Date:
16 September 2005 (online)
Publication History
Publication Date:
16 September 2005 (online)
Abstract
Potassium permanganate supported on manganese(II) sulfate or activated manganese dioxide can be used effectively for the oxidative cleavage of oximes and semicarbazones under solvent-free conditions and for the cleavage of phenylhydrazones in dichloromethane. The residue that remains after extraction of the organic products, primarily manganese oxides, can be recycled, making the process, in theory, infinitely sustainable.
Key words
oximes - semicarbazones - phenylhydrazones - potassium permanganate
- 1
Green TW.Wuts PG. Protective Groups in Organic Synthesis 3rd ed.: John Wiley and Sons; New York: 1991. - 2
Corsaro A.Chiacchio U.Pistara V. Synthesis 2001, 1903 - 3
Barton DHR.Beaton JM. J. Am. Chem. Soc. 1961, 83: 4083 - 4
Kadzyauskas PP.Zefirov NS. Russ. Chem. Rev. (Engl. Transl.) 1968, 37: 543 - 5
Mukai C.Hanaoka M. Synlett 1996, 11 - 6
Czekelius C.Carreira EM. Angew. Chem. Int. Ed. 2005, 44: 612 -
7a
Solid Supports and Catalysts in Organic Synthesis
Smith K. Ellis Harwood and PTR Prentice Hall; New York: 1992. -
7b
Laszlo P. In Comprehensive Organic Synthesis Vol. 7:Trost BM. Pergamon; New York: 1992. p.893 - 8
Shaabani A.Lee DG. Recent Res. Dev. Org. Chem. 2003, 85 - 9
Chrisman W.Blankinship M.Taylor B.Harris CE. Tetrahedron Lett. 2001, 42: 4775 - 10
Hajipour AR.Adibi H.Ruoho AE. J. Org. Chem. 2003, 68: 4553 - 11
Jadhav VK.Wadgaonkar PP.Joshi PL.Salunkhe MM. Synth. Commun. 1999, 29: 1989 - 12
Mohammadpoor-Baltork I.Khodaei MM.Hajipour AR.Aslani E. Monatsh. Chem. 2003, 134: 539 - 13
Singh N.Lee DG. Org. Process Res. Dev. 2001, 5: 599 - 14
Shaabani A.Mirzaei P.Lee DG. Catal. Lett. 2004, 97: 119 - 15
Shaabani A.Mirzaei P.Naderi S.Lee DG. Tetrahedron 2004, 60: 11415 - 16
Alexander EA.Tompkins FC. Trans. Faraday Soc. 1939, 35: 1156 - 17
Kolthoff IM.Sandell EB. Textbook of Quantitative Inorganic Analysis MacMillan; New York: 1955. p.565 - 18
Arndt D. Manganese Compounds as Oxidizing Agents in Organic Chemistry Open Court; La Salle: 1981. Chap. 1. - 19
Shinada T.Yoshihara K. Tetrahedron Lett. 1995, 36: 6701