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Issue 2, 2003
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3-Methylimidazolium bromohydrogenates(I): a room-temperature ionic liquid for ether cleavage

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Abstract

1 H- and 13C{1H}-NMR indicate that the liquid formed at room temperature from 1 mole of 1-methylimidazole and 2 moles of anhydrous HBr contains the 3-methylimidazolium cation (Hmim+) and an equilibrium anionic mixture of Br, HBr2, and H2Br3. This liquid cleaves ethers efficiently, producing the corresponding bromides and alcohols from cyclic and straight-chain dialkyl ethers and phenols and alkyl bromides from aryl alkyl ethers. During the course of the reaction, the single anion proton signal moves several ppm downfield as the [HBr2]/[H2Br3] ratio increases. The nitrogenic proton of Hmim+ is unaffected, confirming that it is not labile and nor is it involved in the reaction, in accord with the large proton affinity of 1-methylimidazole.

Graphical abstract: 3-Methylimidazolium bromohydrogenates(i): a room-temperature ionic liquid for ether cleavage

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Publication details

The article was received on 22 Nov 2002 and first published on 21 Feb 2003


Article type: Paper
DOI: 10.1039/B211548D
Green Chem., 2003,5, 163-169

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    3-Methylimidazolium bromohydrogenates(I): a room-temperature ionic liquid for ether cleavage

    G. Driver and K. E. Johnson, Green Chem., 2003, 5, 163
    DOI: 10.1039/B211548D

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