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 or in the Markó-Lam 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 ^[1] 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.

See also

• Preparation of stable carbenes
• Hydrogen deoxygenation purifier

References

1. ^ Trifluoroacetic anhydride-sodium iodide reagent. Nature and applications Arkivoc 2007 (JE-2136MR) Zbigniew H. Kudzin, Marcin H. Kudzin, Józef Drabowicz, and Andrzej Kotyński Link