Parikh-Doering Oxidation
Автор: Organic Chemistry with Lluís Llorens Palomo
Загружено: 2020-08-08
Просмотров: 2650
Описание:
The Parikh-Doering Reaction is the oxidation of primary and secondary alcohols into aldehydes and ketones. The procedure uses dimethyl sulfoxide (DMSO) as the oxidant, activated by the sulfur trioxide pyridine complex in the presence of triethylamine base.
Reaction mechanism:
1. Activation of DMSO with sulfur trioxide.
2. Nucleophilic attack by the alcohol.
3. Deprotonation of the alkoxysulfonium ion gives the sulfur ylide.
4. The ylide delivers the corresponding ketone and dimethyl sulfide upon rearrangement through a five-membered ring transition state.
Pinterest:
https://www.pinterest.es/pin/67166973...
References:
NROChemistry: https://nrochemistry.com/parikh-doeri...
Seminal publication:
J. Am. Chem. Soc. 1967, 89, 21, 5505–5507. https://doi.org/10.1021/ja00997a067
Similar reactions in organic chemistry:
Swern oxidation: • Swern Oxidation
Ley-Griffith oxidation: • Ley-Griffith Oxidation
Baeyer-Villiger oxidation: • Baeyer-Villiger Oxidation
Corey-Kim oxidation: • Corey-Kim Oxidation
Corey-Gilman-Ganem oxidation: • Corey-Gilman-Ganem Oxidation
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