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Efficient Cleavage of Alkyl Aryl Ethers Using an Ionic Liquid under Microwave Irradiation
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  • Efficient Cleavage of Alkyl Aryl Ethers Using an Ionic Liquid under Microwave Irradiation
  • Efficient Cleavage of Alkyl Aryl Ethers Using an Ionic Liquid under Microwave Irradiation
저자명
Park. Se Kyung,Battsengel. Oyunsaikhan,Chae. Junghyun
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2013년|34권 1호|pp.174-178 (5 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

A highly reliable dealkylation protocol of alkyl aryl ethers, whose alkyl groups are longer than methyl group, has been developed. We report that various ethyl, n-propyl, and benzyl aryl ethers are successfully cleaved using an ionic liquid, 1-n-butyl-3-methylimidazolium bromide, [bmim][Br], under microwave irradiation. Despite many characteristics such as lower cost and less toxicity of the alkylating agents, and greater hydrophobicity of the products, longer alkyl ethers have been significantly less exploited than methyl ethers, probably due to more difficulty in the deprotection step. Since it has the same advantages as the demethylation method developed by this group including mild conditions, short reaction time, and small use of the ionic liquids, the dealkylation protocol can greatly encourage the broader use of longer alkyl groups in the protection of phenolic groups. As with our previous study of demethylation using [bmim][Br], the microwave irradiation is crucial for the deprotection of longer alkyl aryl ethers. Unlike the conventional heating, which causes either low conversion or decomposition, the microwave irradiation seems to more effectively provide energy to cleave the ether bonds and therefore suppresses the undesired reactions.