Information AboutTempo |
| CATEGORIES ABOUT TEMPO | |
| free radicals | |
| nitrogen heterocycles | |
| amine oxides | |
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2,2,6,6-Tetramethylpiperidine-1-oxyl or '''TEMPO''' is the groups adjacent to the nitroxyl group.Zanocco, A. L.; Canetem., A. Y.; Melendez, M. X. ''A Kinetic Study of the Reaction between 2-p-methoxyphenyl-4-phenyl-2-oxazolin-5-one and 2,2,6,6-Tetramethyl-1-piperidinyl-n-oxide'' Bol. Soc. Chil. Quím. 2000 volume 45, pages 123-129. ISSN 0366-1644. APPLICATION IN ORGANIC SYNTHESIS TEMPO is employed in Organic Synthesis as a catalyst for the oxidation of primary Alcohol s to Aldehyde s. The actual oxidant is the N-oxoammonium Salt . In a Catalytic Cycle with Sodium Hypochlorite as the stoichiometric oxidant, Hypochlorous Acid generates the N-oxoammonium salt from the TEMPO. One typical reaction example is the oxidation of (S)-(-)-2-methyl-1-butanol to (S)-(+)-2-methylbutanal.P. L. Anelli, F. Montanari, S. Quici " A General Synthetic Method for the Oxidation of Primary Alcohols to Aldehydes: (S)-(+)-2-Methylbutanal" , being inert towards a secondary alcohols, but the reagent will convert aldehydes to carboxylic acids. In cases where secondary oxidizing agents cause side reactions, it is possible to stoichiometrically convert TEMPO to the oxoammonium salt in a separate step. For example in the oxidation of Geraniol to Geranial 4-acetamido-TEMPO is first oxidized to the oxoammonium tetrafluoroborate.2,6-Octadienal, 3,7-dimethyl-, (2E)- Bobbitt, J. M.; Merbouh, N. Organic Syntheses , Vol. 82, p.80 Online Article REFERENCES EXTERNAL LINKS |
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