Triphenylphosphine oxide

Triphenylphosphine oxide (TPPO) is a chemical compound with the formula OP(C6H5)3. This organic compound is a common byproduct in reactions involving triphenylphosphine. It is a popular reagent in its own right, particularly in the Mitsunobu reaction.

Structure and properties

Triphenylphosphine oxide is a crystalline solid that is colorless or slightly yellow. It is soluble in a variety of organic solvents. The P=O bond is polar, and the oxygen atom is a hydrogen-bond acceptor. The molecule has a tetrahedral molecular geometry around the phosphorus atom.

Preparation

Triphenylphosphine oxide can be prepared by the oxidation of triphenylphosphine, typically with an oxidizing agent such as hydrogen peroxide or a peracid.

Uses

Triphenylphosphine oxide is used as a reagent and a catalyst in organic synthesis. It is particularly known for its use in the Mitsunobu reaction, where it serves as the oxidant for the conversion of primary and secondary alcohols to esters and ethers.

Safety

Like many organophosphorus compounds, triphenylphosphine oxide is considered toxic and should be handled with care. It is also a potential environmental hazard due to its persistence and bioaccumulation.

See also

• Triphenylphosphine
• Mitsunobu reaction
• Organophosphorus compound