Hydrogen‐Bonding Interactions in the Ley–Griffith Oxidation: Practical Considerations for the Synthetic Chemist
| Autor: | Timothy J. Zerk, Peter W. Moore, Craig M. Williams, Paul V. Bernhardt, Jed M. Burns |
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| Rok vydání: | 2018 |
| Předmět: |
Reaction mechanism
Primary (chemistry) 010405 organic chemistry Chemistry Hydrogen bond Organic Chemistry Substrate (chemistry) Alcohol 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Reagent Physical and Theoretical Chemistry |
| Zdroj: | European Journal of Organic Chemistry. 2019:303-308 |
| ISSN: | 1099-0690 1434-193X |
| Popis: | The Ley–Griffith oxidation, which is catalyzed by tetra-n-propylammonium perruthenate (TPAP, nPrN[RuO]), is a popular method for not only controlled oxidation of primary alcohols to aldehydes, but also a host of other synthetically useful transformations. While the fundamental reaction mechanism has recently been elucidated, several key hydrogen-bonding interactions between the reagents were implicated but not investigated. Herein the prevalence of H-bonding between the co-oxidant N-methylmorpholine N-oxide (NMO), the alcohol substrate, water and the perruthenate catalyst is established. These observations help to rationalize the importance of drying the reagents and lead to several practical suggestions. |
| Databáze: | OpenAIRE |
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