Deoxygenation

Deoxygenation is a chemical reaction involving the removal of molecular oxygen (O₂) from a reaction mixture or solvent, or the removal of oxygen atoms from a molecule.

Classic representatives of deoxygenation are:

• the replacement of a hydroxyl group by hydrogen (A-OH → A-H) in the Barton-McCombie deoxygenation
• the replacement of an oxo group by two hydrogen atoms (A=O → A) in the Wolff-Kishner reduction

A chemical reagent for the deoxygenation of many sulfur and nitrogen oxo compounds is the trifluoroacetic anhydride / sodium iodide combination for example in the deoxygenation of the sulfoxide diphenylsulfoxide to the sulfide diphenylsulfide:

Sulfoxide deoxygenation

The reaction mechanism is based on activation of the sulfoxide by a trifluoroacetyl group and oxidation of iodine. Iodine is formed quantitatively in this reaction and therefore the reagent is used for the analytical detection of many oxo compounds.

TFAA NaI deoxygenation mechanism

See also

• Preparation of stable carbenes