Abstract
Results from Hammett correlation studies and primary kinetic isotope effects for the CuCl-TEMPO catalysed aerobic benzyl alcohol oxidations are inconsistent with an oxoammonium based mechanism. We postulate a copper-mediated dehydrogenation mechanism, in which TEMPO regenerates the active Cu(II)-species. This mechanism is analogous to that observed for Galactose Oxidase and mimics thereof.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alcohols / chemistry
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Antioxidants / chemistry
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Benzyl Alcohols / chemistry
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Catalysis
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Chemistry, Organic / methods*
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Copper* / pharmacology
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Cyclic N-Oxides / chemistry
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Galactose Oxidase / chemistry*
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Hydrogen Peroxide / pharmacology
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Kinetics
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Models, Chemical
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Nitrogen Oxides / chemistry*
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Ultraviolet Rays
Substances
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Alcohols
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Antioxidants
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Benzyl Alcohols
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Cyclic N-Oxides
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Nitrogen Oxides
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Copper
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Hydrogen Peroxide
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Galactose Oxidase
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nitroxyl
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cupric chloride
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TEMPO