Efficient Dehydration of Aldoximes to Nitriles Catalyzed by a Lewis Acid Ionic Liquid

A Lewis acid ionic liquid, 1-[4-(chlorosulfonyl)butyl]-3-methylimidazolium chlorosulfate ([CBMIm]SO3Cl), with Lewis acid sites in both the anion and cation was synthesized. This was demonstrated to be an efficient catalyst for dehydration of aldoximes to nitrites. An unexpected self-induced phase se...

Full description

Saved in:
Bibliographic Details
Published inChemistry letters Vol. 40; no. 4; pp. 396 - 397
Main Authors Nakajima, Mizuki, Qiao, Kun, Kobayashi, Nobuhisa, Bao, Quanxi, Tomida, Daisuke, Yokoyama, Chiaki
Format Journal Article
LanguageEnglish
Published TOKYO Chemical Soc Japan 05.04.2011
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
OXIMES
BECKMANN REARRANGEMENT
Online AccessGet more information

Cover

More Information
Summary:A Lewis acid ionic liquid, 1-[4-(chlorosulfonyl)butyl]-3-methylimidazolium chlorosulfate ([CBMIm]SO3Cl), with Lewis acid sites in both the anion and cation was synthesized. This was demonstrated to be an efficient catalyst for dehydration of aldoximes to nitrites. An unexpected self-induced phase separation of the reaction mixture was observed when the reaction was carried out in acetonitrile. This could be attributed to the hydrolysis of [CBMIm]SO3Cl to regenerate 1-(4-sulfo-butyl)-3-methylimidazolium hydrogensulfate ([SBMIm]HSO4), which was the Bronsted precursor of [CBMIm]SO3Cl.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.2011.396