Download Dess-Martin Oxidation

Dess-Martin Oxidation
Muhammad asmael
Dr.Fuad mahmood
contents
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Objectives
Background
Reaction and mechanism
Application and recent literature
Conclusion
reference
objectives
• Dess-Martin periodinane (DMP) is a chemical reagent used to
oxidize primary alcohols to aldehydes and secondary alcohols
to ketones
background
• This periodinane has several advantages over chromium- and
DMSO-based oxidants that include milder conditions (room
temperature, neutral pH), shorter reaction times, higher
yields, simplified workups, high chemoselectivity, tolerance of
sensitive functional groups, and a long shelf life. It is named
after the American chemists Daniel Benjamin Dess and James
Cullen Martin who developed the reagent in 1983. It is based
on IBX, but due to the acetate groups attached to the central
iodine atom, DMP is much more soluble in organic solvents
Reaction and Mechanism
Recent Literature
Acceleration of the Dess-Martin Oxidation by Water
S. D. Meyer, S. L. Schreiber, J. Org. Chem., 1994, 59, 7549-7552.
Recyclable 2nd generation ionic liquids as green solvents for the
oxidation of alcohols with hypervalent iodine reagents
J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron,
2004, 60, 2131-2135.
Application
• In one application of the dess-martin oxidation, involves
transforming a sensitive α-β-unsaturated alcohol to its
corresponding aldehdye.
• This moiety has been found in several natural producs and
due to its high functionality, it could be a valuable synthetic
building block in organic synthesis.
conclusion
• Iubac name for dess martin oxidation
1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one
• The Baylis–Hillman adducts of aryl aldehydes and alkyl
acrylates are efficiently oxidized to the corresponding αmethylene-β-keto esters with the Dess–Martin periodinane.
Reference
• http://www.organic-chemistry.org/namedreactions/dessmartin-oxidation.shtm
• ^ Dess, D. B.; Martin, J. C. (1983). "Readily accessible 12-I-5
oxidant for the conversion of primary and secondary alcohols
to aldehydes and ketones". J. Org. Chem. 48: 4155.
doi:10.1021/jo00170a070.
• Boeckman, R. J. In "Encyclopedia of Reagents for Organic
Synthesis"; Paquette, L. A., Ed.; Wiley: Chichester, UK, 1995,
Vol. 7, pp. 4982-4987. (Review)
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