Swern Oxidation

RCH2OH + (COCl)2 + DMSO → RCHO + DMS + CO2 + CO + 2HCl

概述

The Swern oxidation converts primary and secondary alcohols to aldehydes and ketones using DMSO activated by oxalyl chloride, followed by base (triethylamine). It operates at -78 C (dry ice/acetone) to prevent side reactions. This mild, chromium-free method is preferred for sensitive substrates.

日常示例

The Swern oxidation replaced toxic chromium reagents in many pharmaceutical syntheses, making drug manufacturing safer.

工业重要性

Swern氧化在制药合成中广泛用于复杂天然产物和药物中间体的醇→醛/酮选择性氧化，条件温和不消旋。

属性

类型
Organic
可逆
否
能量
放热
ΔH
-120.0 kJ/mol

相关反应

Epoxidation of Alkenes (mCPBA) Oxidation of Secondary Alcohol to Ketone E2 Elimination (Dehydrohalogenation) Claisen Condensation (Ethyl Acetate) Aldol Condensation of Acetaldehyde Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Dehydration of Ethanol

Frequently Asked Questions

What is the equation for Swern Oxidation?
The balanced equation is: RCH₂OH + (COCl)₂ + DMSO → RCHO + DMS + CO₂ + CO + 2HCl.
What type of reaction is Swern Oxidation?
Swern Oxidation is a organic reaction.
Is Swern Oxidation exothermic or endothermic?
Swern Oxidation is exothermic (releases energy). The enthalpy change (ΔH) is -120.0 kJ/mol.