Dess–Martin periodinane

Dess–Martin periodinane (DMP) is an organic compound used primarily as an oxidizing agent in organic synthesis. Developed by Daniel Benjamin Dess and James Cullen Martin in 1983, DMP has become a popular choice for selectively oxidizing primary alcohols to aldehydes and secondary alcohols to ketones with minimal overoxidation to carboxylic acids. Its chemical formula is C₁₃H₁₅IO₇.

Properties

Dess–Martin periodinane is characterized by its stability and mildness as an oxidizing agent. Unlike other oxidizing agents, DMP operates under relatively mild conditions, thus preserving sensitive functional groups in the substrate. It is a white to off-white crystalline solid, soluble in organic solvents such as dichloromethane, chloroform, and acetonitrile.

Synthesis

The synthesis of Dess–Martin periodinane involves the reaction of Iodoxybenzoic acid (IBX) with 1,1,1-triisopropylbenzene under acidic conditions to yield DMP. This process highlights the transformation of IBX, a potent oxidizing agent in its own right, into a more selective and user-friendly reagent.

Mechanism

The mechanism of action for DMP involves the formation of an iodonium ion intermediate, which facilitates the transfer of an oxygen atom to the alcohol substrate. This results in the formation of the desired ketone or aldehyde product and the reduction of DMP to iodylbenzene diacetate, which can be easily separated from the reaction mixture.

Applications

Dess–Martin periodinane has found widespread use in organic synthesis, including the synthesis of complex natural products and pharmaceuticals. Its ability to selectively oxidize alcohols without affecting other functional groups makes it an invaluable tool in the chemist's toolkit. DMP is particularly useful in the final steps of synthesis, where the selective oxidation of a primary or secondary alcohol can be crucial to obtaining the desired product.

Safety and Handling

While Dess–Martin periodinane is considered less hazardous than many other oxidizing agents, it should still be handled with care. Precautions should be taken to avoid inhalation and contact with skin or eyes. Use in a well-ventilated area and personal protective equipment such as gloves and goggles are recommended.

Environmental Considerations

The use of DMP in organic synthesis poses minimal environmental risk when used and disposed of properly. However, as with all chemical reagents, responsible use and disposal practices should be followed to minimize any potential environmental impact.

See Also

• Oxidizing agent
• Organic synthesis
• Iodoxybenzoic acid
• Alcohol oxidation

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Dess–Martin periodinane

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  Dess–Martin periodinane

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  Dess–Martin periodinane 3D model

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  Reaction scheme

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  Preparation of DMP

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  Dess–Martin synthesis

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  Oxidation by Dess–Martin periodinane

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  Water addition

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  Dess–Martin periodinane oxidation

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  T-butyl DMP