1 / 9

DESS-MARTIN OXIDATION

DESS-MARTIN OXIDATION. ——By D.B. Dess and J.C. Martin. Importance. Importance. Since the early 1980s, hypervalent iodine reagents have emerged as selective, mild, and environmentally friendly oxidizing agents in organic synthesis.

jamesma
Download Presentation

DESS-MARTIN OXIDATION

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. DESS-MARTIN OXIDATION ——By D.B. Dess and J.C. Martin

  2. Importance

  3. Importance Since the early 1980s, hypervalent iodine reagents have emerged as selective, mild, and environmentally friendly oxidizing agents in organic synthesis. In 1983, D.B. Dess and J.C. Martin reported the preparation of 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (DMP) via the acylation of IBX. This new periodinane is far more soluble in organic solvents than IBX; since its discovery it has emerged as the reagent of choice for the oxidation of alcohols to the corresponding carbonyl compounds. Oxidations using DMP are called Dess-Martin oxidations.

  4. Advantages • mild reaction conditions (roomtemperature, neutral pH) • high chemoselectivity • tolerance of sensitive functional groups on complex substrates • long shelf-life and thermal stability

  5. Mechanism When excess alcohol is present, the oxidation is much faster due to the especially labile nature of acetoxydialkoxyperiodinanes. It has also been shown that added water accelerates DMP oxidations

  6. Synthetic Applications

  7. Synthetic Applications

  8. Synthetic Applications

More Related