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Unexpected course of the reaction of 2-Unsubstituted 1H-Imidazole 3-Oxides with Ethyl Acrylate


Mloston, G; Urbaniak, K; Wojciechowska, A; Linden, A; Heimgartner, H (2012). Unexpected course of the reaction of 2-Unsubstituted 1H-Imidazole 3-Oxides with Ethyl Acrylate. Helvetica Chimica Acta, 95(4):577-585.

Abstract

The attempted ethenylation at C(2) of 2-unsubstituted 1H-imidazole N-oxides with ethyl acrylate (= prop-2-enoate) in the presence of Pd(OAc)2 does not occur. In contrast to the other aromatic N-oxides, the [2+3] cycloaddition of imidazole N-oxides predominates, and 3-hydroxyacrylates, isomeric with the cycloadducts, are key products for the subsequent reaction. The final products were identified as dehydrated 2+1 adducts of 1H-imidazole N-oxide and ethyl acrylate. The role of the catalyst is limited to the dehydration of the intermediate 3-hydroxypropanoates to give 1H-imidazol-2-yl-substituted acrylates.

Abstract

The attempted ethenylation at C(2) of 2-unsubstituted 1H-imidazole N-oxides with ethyl acrylate (= prop-2-enoate) in the presence of Pd(OAc)2 does not occur. In contrast to the other aromatic N-oxides, the [2+3] cycloaddition of imidazole N-oxides predominates, and 3-hydroxyacrylates, isomeric with the cycloadducts, are key products for the subsequent reaction. The final products were identified as dehydrated 2+1 adducts of 1H-imidazole N-oxide and ethyl acrylate. The role of the catalyst is limited to the dehydration of the intermediate 3-hydroxypropanoates to give 1H-imidazol-2-yl-substituted acrylates.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:April 2012
Deposited On:20 Apr 2012 07:04
Last Modified:07 Dec 2017 13:50
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.201100519

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