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

Oxidation of Secondary Alcohol to Ketone Claisen Condensation (Ethyl Acetate) Kolbe Electrolysis Baeyer-Villiger Oxidation Beckmann Rearrangement (Cyclohexanone Oxime) Catalytic Hydrogenation of Ethylene Condensation Polymerization (Nylon 6,6) Cope Rearrangement Oxidation of Primary Alcohol to Aldehyde Epoxidation of Alkenes (mCPBA)

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.