Cr(VI)-pyridine and pyridinium reagents have the advantage that they are soluble in organic solvents as are the alcohol substrates.
This process is postulated to occur via initial oxidation of the alcohol, attack of the alkene on the new carbonyl, then re-oxidation to a ketone.
[1] An important process mediated by chromium(VI)-amines is the oxidative transposition of tertiary allylic alcohols to give enones.
[1] Enones can be synthesized from tertiary allylic alcohols through the action of a variety of chromium(VI)-amine reagents, in a reaction known as the Babler oxidation.
[1] In addition to the limitations described above, chromium(VI) reagents are often unsuccessful in the oxidation of substrates containing heteroatoms (particularly nitrogen).
Coordination of the heteroatoms to chromium (with displacements of the amine ligand originally attached to the metal) leads to deactivation and eventual decomposition of the oxidizing agent.
[6] Dess-Martin periodinane (DMP) offers the advantages of operational simplicity, a lack of heavy metal byproducts, and selective oxidation of complex, late-stage synthetic intermediates.