Oxidation with chromium(VI) complexes: Difference between revisions

Revision as of 23:50, 23 June 2010

Revision as of 23:51, 23 June 2010

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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, D. B.; Martin, J. C. ''J. Org. Chem.'', '''1983''', ''48'', 4156.</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 cheapercheap, clean terminal oxidants in conjunction with catalytic amounts of chromium reagents offerproduce the benefit ofonly 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.

==Experimental Conditions and Procedure==