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SWERN OXIDATION
CHE-MYSTERY
Subscribe
NAVEEN K
II-M.Sc CHEMISTRY,
St. JOSEPH’S COLLEGE(AUTONOMOUS),
TRICHY-620002.
SWERN OXIDATION
• The Swern Oxidation of alcohols avoids the use of toxic metals such as
chromium, and can be carried out under very mild conditions.
• This reaction allows the preparation of aldehydes and ketones from
primary and secondary alcohols, respectively. Aldehydes do not react
further to give carboxylic acids.
• A drawback is the production of the malodorous side product
dimethyl sulphide.
MECHANISM
The reaction with an alcohol at -78°C leads to an alkoxysulphonium ion:
• If the temperature is not kept near -78°C, mixed thioacetals may
result:
EXAMPLE
• No enolization takes place. So, stereochemistry is maintained.
THANK YOU
CHE-MYSTERY
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Swern oxidation