Dess-Martin periodinane
DMP
1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one
BUJNO Synthesis Sp. z o. o.
Dorodna 16
03-195 Warszawa, POLAND
www.bujno.com.pl

 
CAS: 87413-09-0 DMP
FW: 424,16
Melting point: 133-134 oC
Merck: 13,2950
Beilstein: 4548207
The Dess-Martin periodinane (DMP) is a mild, versatile reagent for selective oxidation of primary and secondary alcohols to aldehydes and ketones, hydroxamic acids to acyl notroso compounds, deprotection of thioacetals, deoximation of ketoximes to ketones.

  Preparations of Dess-Martin Periodinane
  • Readily Accessible 12-I-5 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones,
    Dess, D.B., Martin, J.C., J. Org.Chem. 48 (1983) 4155.
  • A Useful 12-I-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species,
    Daniel B. Dess and J.C. Martin, J.Am.Chem.Soc., 113 (1991) 7277.
  • An Improved Procedure for the Preparation of the Dess-Martin Periodinane,
    Robert E. Ireland and Longbin Liu, J.Org.Chem., 58 (1993) 2899.
  • A User-Friendly Entry to 2-Iodoxybenzoic acid (IBX),
    Marco Frigerio and Marco Santagostino and Simona Sputore, J.Org.Chem., 64 (1999) 4537.
  • Magnesium amide base-mediated enantioselective deprotonation processes,
    Kenneth W. Henderson, William J. Kerr and Jennifer H. Moir, Tetrahedron, 58 (2002)4573.

  Applications of Dess-Martin Periodinane
  • Readily Accessible 12-I-5 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones,
    Dess, D.B., Martin, J.C., J. Org.Chem. 48 (1983) 4155.
  • Enatioselective Total Synthesis of (-)-Preclavulone-A,
    E.J. Corey and Yi Bin Xiang, Tetrahedron Lett., 29 (1988) 995.
  • Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent,
    Russell J. Linderman and David M. Grave, J.Org.Chem., 54 (1989), 661.
  • Development of a Fully Synthetic Stereoselective Route to 6-Deoxyerythronolide B by Reiterative Applications of the Lewis Acid Catalyzed Diene Aldehyde Cyclocondensation Reaction: A Remarkable Instance if Diastereofacial Selectivity,
    David C. Myles and Samuel J. Danishefsky, J.Org.Chem., 55 (1990) 1636.
  • A Useful 12-I-5 Triacetoxyperiodinane (the Dess-Martin Periodinane) for Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related 12-I-5 Species,
    Daniel B. Dess and J.C. Martin, J.Am.Chem.Soc., 113 (1991) 7277.
  • A Novel Application of the Dess-Matrin Reagent to the Synthesis of an FK506 Analogue and other Tricarbonyl Compounds,
    Mark J. Batchelor, Roger J. Gillespie, Julian M.C. Golec and Charles J. R. Hedgecock, Tetrahedron Lett., 34 (1993) 167.
  • Hypervalent Iodine Oxidant: Structure and Kinetics of the reactive Intermediates in the Oxidation of Alcohols an 1,2-Diols by o-Iodoxybenzoic acid (IBX) and Dess-Martin Periodinane. A Comparative H-NMR study.
    Sergio De Munari, Marco Frigerio and Marco Santagostino, J.Org.Chem., 61 (1996) 9272.
  • The Asymetric Synthesis of Erythromycin B,
    Stephen F. Martin, Tsuneki Hida, Philip R. Kym, Michael Loft and Anne Hodgson, J.Am.Chem.Soc., 119 (1997) 3193.
  • Deoximation Using Dess-Martin Periodinane: Regeneration of Ketones from Ketoximes,
    Sachin S. Chaudhari and Krisshnacharya G. Akamanchi, Tetrhedron Lett., 39 (1998) 3209.
  • Reaction of 1,1,1-Trifluoro[chloro]-4-ethoxybut-3-en-2ones with 1,3-Dicarbonyl Compounds: Synthesis of 5-Acetyl[carboxyethyl]-1,1,1-trifluoro[chloro]hept-3-ene-2,6-diones and their Cyclic Derivatives Phenol, Pyridines and Azetone,
    Nilo Zanatta, Resemario Barichello, Helio G. Bonacorso, Marcos A.P. Martins, Synthesis, 5 (1999) 765.
  • New Synthetic Technology for the Rapid Construction of Novel Heterocycles- Part1: The Reaction of Dess-Martin Periodinane with Anilides and Related Compounds,
    K.C. Nicolaou, Young-Li Zhong, Phil S. Baran, Angew. Chem.Int.Ed, 39 (2000) 622.
  • New Synthetic Technology for the Rapid Construction of Novel Heterocycles- Part2: The Reaction of Dess-Martin Periodinane with Anilides and Related Compounds,
    K.C. Nicolaou, Young-Li Zhong, Phil S. Baran, Angew. Chem.Int.Ed, 39 (2000) 625.
  • Oxidation of a,v-Diols Using the Dess-Martin Periodinane,
    Jochen Roels, Peter Metz, Synlett, 6 (2001) 789.
  • A Mild, Chemoselective Protocol for the Removal of Thioketals and Thioacetals Mediated by Dess-Martin Periodinane,
    Neil F. Langille, Less A. Dakin, and James S. Panek, Org.Lett., 5 (2003) 575.
  • Shotgun Process through Differentiation of Aliphatic and Aromatic Aldehyde Functions: The First Synthesis of Ferulic Acid Hexan-3-onyl Ether,
    Yoshifumi Nagano, Akhiro Orita, Junzo Otera, Synlett, 5 (2003) 684.
  • Preparation of 14,36-didehydro pristinamycins IIs,
    Baptiste Ronan, Eric Bacque, Jean-Claude Barriere and Serge Sable, Tetraherdon, 59 (2003) 2929.
  • Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents,
    J.S. Yadav, B.V.S. Redy, A.K. Basak and A. Venkat Narsaiah, Tetrahedron, 60 (2004) 2131.
  • Synthesis of Imides, N-Acyl Vinylogous Carbamates and Ureas, and Nitriles by Oxidation of Amides and Amines with Dess-Martin Periodinane,
    K.C. Nicolaou and Casey J.N. Mathison, Angew.Chem.Int.Ed, 44 (2005) 5992.
  • Syntheses of the cylindrospermopsin alkaloids,
    Ryan E. Looper, Maria T.C. Runnegar and Robert M. Williams, Tetrahedron, 62 (2006) 4549.
  • Hypervalent Iodine Mediated Intramolecular Cyclization of Thioformanilides: Expeditous Approach to 2-Substituted Benzothiazoles,
    D.Subhas Bose and Mohd. Idrees, J.Org.Chem., 71 (2006) 8261.

  Spectral properties of Dess-Martin Periodinane
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