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Dess-Martin periodinane

 

 
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Dess-Martin periodinane
 
 
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Dess-Martin periodinane is a chemical reagent used to oxidize primary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s and secondary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s. This periodinane
Periodinane

Periodinanes are chemical compounds containing hypervalent iodine. These iodine compounds are hypervalency because the iodine atom in it contains more than the 8 electrons in the valence shell required for the octet rule....
 has several advantages over chromium
Chromium

Chromium is a chemical element which has the symbol Cr and atomic number 24. It is a steely-gray, Lustre , hard metal that takes a high polish and has a high melting point....
- and DMSO
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin
James Cullen Martin

James Cullen Martin was a American chemist.He discovered together with Daniel Benjamin Dess the Dess-Martin periodinane.Reference*...
.

dobenzoic acid is oxidized preferably by Oxone, or by KBrO3 to 2-iodoxybenzoic acid
2-Iodoxybenzoic acid

IBX acid or 2-Iodoxybenzoic acid is an organic compound used in organic synthesis as an oxidizing agent. This Periodinane is especially suited to organic oxidation alcohols to aldehydes....
.






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Encyclopedia


Dess-Martin periodinane is a chemical reagent used to oxidize primary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
s and secondary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
s. This periodinane
Periodinane

Periodinanes are chemical compounds containing hypervalent iodine. These iodine compounds are hypervalency because the iodine atom in it contains more than the 8 electrons in the valence shell required for the octet rule....
 has several advantages over chromium
Chromium

Chromium is a chemical element which has the symbol Cr and atomic number 24. It is a steely-gray, Lustre , hard metal that takes a high polish and has a high melting point....
- and DMSO
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin
James Cullen Martin

James Cullen Martin was a American chemist.He discovered together with Daniel Benjamin Dess the Dess-Martin periodinane.Reference*...
.

Preparation

2-Iodobenzoic acid is oxidized preferably by Oxone, or by KBrO3 to 2-iodoxybenzoic acid
2-Iodoxybenzoic acid

IBX acid or 2-Iodoxybenzoic acid is an organic compound used in organic synthesis as an oxidizing agent. This Periodinane is especially suited to organic oxidation alcohols to aldehydes....
. (Caution: 2-Iodoxybenzoic acid has been found to be impact and heat sensitive, decomposing explosively.) The 2-Iodoxybenzoic acid is then treated with a mixture of acetic anhydride
Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
, acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
 and p-toluenesulfonic acid
P-Toluenesulfonic acid

p-Toluenesulfonic acid is an organic compound with the formula methyl groupbenzeneSulfonic acid. TsOH, as it is abbreviated, is a white solid that is soluble in water, alcohols, and other Chemical polarity organic solvents....
 at 80-100 °C for 40 min. The resulted solids can be obtained via filtration
Filtration

Filtration is a mechanical or physical operation which is used for the separation of solids from fluids by interposing a medium to fluid flow through which the fluid can pass, but the solids in the fluid are retained....
 and washing with ether
Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
.

To avoid the explosive nature of 2-iodoxybenzoic acid, other methods of preparation as well as other periodinanes have been described.

Properties and uses

Dess-Martin periodinane is mainly used as an oxidant for complex, sensitive and multifunctional alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s. One of the reasons for its effectiveness is its high selectivity towards complexation of the hydroxylic
Hydroxide

In chemistry, hydroxide is the name for the Diatomic molecule anion OH-, consisting of oxygen and hydrogen atoms, usually derived from the Dissociation of a base ....
 group, which allows alcohols to rapidly perform ligand
Ligand

In chemistry, a ligand is either an atom, ion, or molecule that bonds to a central metal, generally involving formal donation of one or more of its electrons....
 exchange; the first step in the oxidation reaction.

Its effectiveness as an oxidant is also due to its versatility; having a broad scope of being able to convert alcohols to carbonyl
Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
 derivatives. Its reactions and yield are also known to be clean and high respectively. Work up is also clean and simple. Byproducts from the reaction can be removed easily by precipitation, filtration or chromatography
Chromatography

Chromatography is the collective term for a family of laboratory techniques for the separation of mixtures. It involves passing a mixture dissolved in a "mobile phase" through a stationary phase, which separates the analyte to be measured from other molecules in the mixture and allows it to be isolated....
.

See also

  • Pyridinium chlorochromate
    Pyridinium chlorochromate

    Pyridinium chlorochromate is a reddish orange solid reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Pyridinium chlorochromate, or PCC, will not fully oxidize the alcohol to the carboxylic acid as does the Jones reagent....