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Synthesis 2017; 49(12): 2721-2726
DOI: 10.1055/s-0036-1588755
DOI: 10.1055/s-0036-1588755
paper
Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers
Further Information
Publication History
Received: 23 January 2017
Accepted after revision: 27 February 2017
Publication Date:
14 March 2017 (online)
Abstract
A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for the coupling of amines and carboxylic acids to yield amide bonds, are found to be effective hydrogen iodide scavengers that prevent acid-labile groups from deterioration. The method is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho-vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o-hydroxyphenyl ethers.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588755.
- Supporting Information
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