Oxidation of Secondary Methyl Ethers to Ketones

[Image: see text] We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketone...

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Autores principales: Gilissen, Pieter J., Blanco-Ania, Daniel, Rutjes, Floris P. J. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5504491/
https://www.ncbi.nlm.nih.gov/pubmed/28585818
http://dx.doi.org/10.1021/acs.joc.7b00632
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author Gilissen, Pieter J.
Blanco-Ania, Daniel
Rutjes, Floris P. J. T.
author_facet Gilissen, Pieter J.
Blanco-Ania, Daniel
Rutjes, Floris P. J. T.
author_sort Gilissen, Pieter J.
collection PubMed
description [Image: see text] We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.
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spelling pubmed-55044912017-07-12 Oxidation of Secondary Methyl Ethers to Ketones Gilissen, Pieter J. Blanco-Ania, Daniel Rutjes, Floris P. J. T. J Org Chem [Image: see text] We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group. American Chemical Society 2017-06-06 2017-07-07 /pmc/articles/PMC5504491/ /pubmed/28585818 http://dx.doi.org/10.1021/acs.joc.7b00632 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Gilissen, Pieter J.
Blanco-Ania, Daniel
Rutjes, Floris P. J. T.
Oxidation of Secondary Methyl Ethers to Ketones
title Oxidation of Secondary Methyl Ethers to Ketones
title_full Oxidation of Secondary Methyl Ethers to Ketones
title_fullStr Oxidation of Secondary Methyl Ethers to Ketones
title_full_unstemmed Oxidation of Secondary Methyl Ethers to Ketones
title_short Oxidation of Secondary Methyl Ethers to Ketones
title_sort oxidation of secondary methyl ethers to ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5504491/
https://www.ncbi.nlm.nih.gov/pubmed/28585818
http://dx.doi.org/10.1021/acs.joc.7b00632
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AT blancoaniadaniel oxidationofsecondarymethyletherstoketones
AT rutjesflorispjt oxidationofsecondarymethyletherstoketones

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