Swern Oxidation

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

개요

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.

일상 속 예시

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

산업적 중요성

스워른 산화는 온화한 조건, 선택성, 독성 중금속 회피로 인해 의약품 공정 화학에서 널리 사용됩니다.

성질

유형
Organic
가역 반응
아니오
에너지
발열
ΔH
-120.0 kJ/mol

관련 반응

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.