Transformation of epoxides into halohydrins and aminoalcohols by metal halides
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Title Transformation of epoxides into halohydrins and aminoalcohols by metal halides
Creator Sirinuch Pattarativanont
Contributor Warinthorn Chavasiri
Publisher Chulalongkorn University
Publication Year 2550
Keyword อิพอกไซด์, สารประกอบอีพอกซี, แฮโลไฮดริน, อะมิโนแอลกอฮอล์, โลหะแฮไลด์, Epoxide, Epoxy compounds, Halohydrin, Aminoalcohol, Metal halides
Abstract This work focuses on the development of an efficient procedure for the selective ring opening of substituted epoxides under mild and rapid conditions utilized either chromium(III) chloride or chromium(III) nitrate. The ring opening of alkyl- and aryl-substituted epoxides with these chromium(III) reagents produced halohydrin and aminoalcohol in high to excellent yield. Regioselectivity for a C-O bond cleavage of epoxide via Lewis acid promoted was greatly depended on the substitution pattern of epoxides furnished halohydrins and aminoalcohols through a predominantly SN2-type mechanism. This procedure is very simple, mild, rapid, commercially available, inexpensive, insensitive to air and high selectivity of product compared to those catalyzed by other Lewis acids.
URL Website cuir.car.chula.ac.th
Chulalongkorn University

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