Dess-Martin Oxidation

1
Dess-Martin Oxidation
??? ???? ?????? ??????An-Najah National
University

• Prepared By Muhammad Asmael
• Supervisor Fuad Mahmmod
• Name of course research chemistry

2
contents

• Objectives
• Background
• Reaction and mechanism
• Application and recent literature
• Conclusion
• reference

3
objectives

• Dess-Martin periodinane (DMP) is a chemical
  reagent used to oxidize primary alcohols to
  aldehydes and secondary alcohols to ketones

4
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

5
Reaction and Mechanism
6
Recent Literature
Acceleration of the Dess-Martin Oxidation by
WaterS. 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 reagentsJ. S. Yadav, B. V. S.
Reddy, A. K. Basak, A. V. Narsaiah, Tetrahedron,
2004, 60, 2131-2135.
7
Application

• In one application of the dess-martin oxidation,
  involves transforming a sensitive a-ß-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.
• Thongsornkleeb and Danheiser oxidized this
  sensitive alcohol by employing the Dess Martin
  Oxidation and altering the work up procedure
  (diluting with pentanes, washing with
  poly(4-vinylpyridine) to remove the acetic acid
  generated during the reaction, filtering and
  concentrating via distillation.14

8
(No Transcript)
9
conclusion

• Iubac name for dess martin oxidation
• 1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)
  -one

10
Reference

• http//www.organic-chemistry.org/namedreactions/de
  ss-martin-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.
  doi10.1021/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)

11

• Thank You For Listening