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:



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.