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Dimethyl Sulfoxide Oxidation of an Alcohol

Step 1 The alcohol reacts with the active oxidizing agent, chlorodimethylsulfonium ion, previously generated by the reaction between dimethyl sulfoxide and oxalyl chloride. The oxygen of the alcohol displaces chloride from sulfur. [Pg.666]

Step 2 The conjugate acid of the alkoxydimethylsulfonium ion is deprotonated by chloride. [Pg.666]

Step 3 Triethylamine is added to the reaction mixture and acts as a base to remove a proton from one of the 5-methyl groups of the alkoxydimethylsulfonium ion. The product of this reaction is an ylide—a neutral molecule in which two directly bonded atoms, each with an octet of electrons, are oppositely charged. [Pg.666]

Step 4 Intramolecular proton abstraction from the H—C—O unit by the negatively charged carbon triggers dissociation of the ylide to an aldehyde or ketone and dimethyl sulfide. [Pg.666]

Many biological processes involve oxidation of alcohols to carbonyl compounds or the reverse process, reduction of carbonyl compounds to alcohols. Ethanol, for example, is metabolized in the liver to acetaldehyde in a reaction catalyzed by the enzyme alcohol [Pg.666]


Dimethyl Sulfoxide Oxidation of an Alcohol (Swern Oxidation) 666 Oxidation of Ethanol by NAD 669... [Pg.646]


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6,6-Dimethyl 1-oxid

Alcohols dimethyl sulfoxide

Dimethyl sulfoxide oxidations

Of 2.2-dimethyl

Of dimethyl sulfoxide

Sulfoxide oxidation

Sulfoxides dimethyl

Sulfoxides dimethyl sulfoxide

Sulfoxides oxidation

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