Dess–Martin periodinane

1,1,1- triacetoxy -1 ,1- dihydro -1 ,2- benziodoxol -3 ( 1H)-one

Fixed

1.36 g · cm -3

133-134 ° C

Attention

Not assigned because evidence of a carcinogenic effect

873 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Dess- Martin periodinane is a chemical compound which is used in organic synthesis for oxidizing primary alcohols to aldehydes and secondary alcohols to ketones. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin. To oxidizing agents to chromium - or DMSO - based ( Jones or Swern oxidation ) Dess- Martin periodinane has several advantages. In addition to milder conditions, lower toxicity, shorter reaction times and higher yields are also a simpler working-up after the reaction.

Synthesis

The synthesis starts from 2- iodobenzoic acid, which in the first step by means of potassium IBX ( 1-hydroxy -1 ,2- benziodoxol -3 ( 1H)-one -1-oxide ) is oxidized. The target molecule is obtained in the second step by acylation with acetic anhydride and acetic acid.

Properties

The compound is thermally unstable. When heated under confinement at temperatures from 130 ° C may lead to explosive decomposition. In the presence of water or humidity hydrolysis to IBX done.

Use

Dess- Martin periodinane is used for the Dess-Martin oxidation.