Oxidation with chromium(VI) complexes: Difference between revisions

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==Comparison with other methods==

Methods employing dimethyl sulfoxide (the [[Swern oxidation|Swern]] and [[Moffatt oxidation]]s) are superior to chromium(VI)-amines for oxidations of substrates with heteroatom functionality that may coordinate to chromium.<ref>Tidwell, T. ''Org. React.'' '''1990''', ''39'', 297.</ref> [[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.<ref>Dess,{{cite D.journal B|doi=10.; Martin1002/047084289X.rt157m.pub2|title=1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one|journal=Encyclopedia J.of C.Reagents ''J.for Org.Organic Synthesis|year=2009|last1=Boeckman|first1=Robert ChemJ.'', '''1983''', ''48'',|last2=George|first2=Kelly 4156M.}}</ref> Additionally, both DMP and [[manganese dioxide]] (MnO₂) can be used to oxidize allylic alcohols to the corresponding enones without allylic transposition. When allylic transpositions is desired, however, chromium(VI)-amine reagents are unrivaled.

Catalytic methods employing cheap, clean terminal oxidants in conjunction with catalytic amounts of chromium reagents produce only small amounts of metal byproducts.<ref>Muzart, J. ''Tetrahedron Lett.'', '''1987''', ''28'', 2133.</ref> However, undesired side reactions mediated by stoichiometric amounts of the terminal oxidant may occur.