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Oxoammonium-catalyzed oxidation
Oxoammonium-catalyzed oxidation reactions involve the conversion of organic substrates to more highly oxidized materials through the action of an N-oxoammonium species. Nitroxides may also be used in catalytic amounts in the presence of a stoichiometric amount of a terminal oxidant.〔Bobbitt, J. M.; Bruckner, C.; Merbouh, N. ''Org. React.'' 2009, ''74'', 103. 〕
==Introduction==
The first discovery of a stable nitroxide radical was made in 1959.〔Lebedev, O. A.; Kazarnovskii, S. N. ''Trudy po Khimii i Khim. Technologii (Gorkii)'' 1959, ''8'', 649.〕 Since then, they have been developed as a versatile class of organic oxidants, both in the stoichiometric and catalytic mode. A single-electron oxidation of the nitroxide radical produces a highly electrophilic oxoammonium species, which serves as the active oxidizing agent. Although pre-formed ''N''-oxoammonium salts may be used stoichiometrically for oxidations,〔Merbouh, N.; Bobbitt, J. M.; Brückner, C. ''J. Org. Chem.'' 2004, ''69'', 5116.〕 these have largely been replaced by catalytic methods that use a cheaper terminal oxidant, such as sodium hypochlorite or bis(acetoxy)iodobenzene (BAIB).〔 Nitroxide radical species used are either 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) or derivatives thereof. Examples of oxoammonium-based oxidations are shown below.
''(1)''File:OxoamGen.png
抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』
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