- Aldehyde
- Ganem oxidation
- Kornblum oxidation
- List of organic reactions
- Elias James Corey
- Oxoammonium-catalyzed oxidation
- Potassium permanganate
- Madeira
- Quaternary ammonium cation
- Protecting group
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In organic chemistry, the Ganem oxidation is a name reaction that allows for the preparation of carbonyls from primary or secondary alkyl halides with the use of trialkylamine N-oxides, such as N-methylmorpholine N-oxide or trimethylamine N-oxide.
Mechanism
As in other oxoammonium-catalyzed oxidation reactions, the negatively charged oxygen atom of the trialkylamine N-oxide molecule attacks the alkyl halide in a SN2 manner, kicking of the halide as a leaving group. A trialkylamine deprotonates the α-carbon atom, the resulting electron pair shifts onto the oxygen atom, which shifts its own excess electron pair onto the nitrogen atom. This generates the desired carbonyl, as well as the aforementioned trialkylamine. The reaction is an enhancement of the Kornblum oxidation protocol, which was originally developed using dimethyl sulfoxide or pyridine-N-oxide as the nucleophile.
Applications
The Ganem oxidation has been used as an intermediate step in the total synthesis of (−)-okilactomycin, converting a primary alkyl halide into an aldehyde.
References
Kata Kunci Pencarian:
Ganem Oxidation
Corey-Gilman-Ganem Oxidation - nrochemistry.com
Corey-Gilman-Ganem Oxidation - nrochemistry.com
Corey-Gilman-Ganem Oxidation - nrochemistry.com
Corey-Gilman-Ganem Oxidation - nrochemistry.com
Corey-Gilman-Ganem Oxidation - nrochemistry.com
Ganem Oxidation - ALL ABOUT CHEMISTRY
Ganem Oxidation ALL ABOUT CHEMISTRY
Corey-Gilman-Ganem Oxidation | Chem-Station Int. Ed.
Corey-Gilman-Ganem Oxidation | Chem-Station Int. Ed.
Corey-Gilman-Ganem Oxidation | Chem-Station Int. Ed.
Corey-Gilman-Ganem Oxidation | Chem-Station Int. Ed.