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Issue 15, 2013
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Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis

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Abstract

For too long the aromatic aza-Claisen rearrangement has been the poor relation of its oxygen counterpart. We demonstrate that on-water catalysis facilitates the rearrangement of reverse N-prenylated naphthylamines and anilines, and transforms the aromatic aza-Claisen rearrangement into a synthetically viable reaction. We use this reaction to probe the mechanism of on-water catalysis, and provide compelling support for the acid-catalysis hypothesis.

Graphical abstract: Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis

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Publication details

The article was received on 21 Jan 2013, accepted on 08 Feb 2013 and first published on 11 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB40118A
Citation: Org. Biomol. Chem., 2013,11, 2452-2459
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    Revitalizing the aromatic aza-Claisen rearrangement: implications for the mechanism of ‘on-water’ catalysis

    K. D. Beare and C. S. P. McErlean, Org. Biomol. Chem., 2013, 11, 2452
    DOI: 10.1039/C3OB40118A

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