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Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions

The acyl nitroso Diels–Alder reaction of 1,3‐dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro‐induced decomposition could be suppressed in favour of the 1,2‐oxazine cycloaddition products. The reaction was optimise...

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Autores principales: Fährmann, Jan, Hilt, Gerhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456936/
https://www.ncbi.nlm.nih.gov/pubmed/34232547
http://dx.doi.org/10.1002/anie.202107148
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author Fährmann, Jan
Hilt, Gerhard
author_facet Fährmann, Jan
Hilt, Gerhard
author_sort Fährmann, Jan
collection PubMed
description The acyl nitroso Diels–Alder reaction of 1,3‐dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro‐induced decomposition could be suppressed in favour of the 1,2‐oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3‐dienes and hydroxamic acids, giving up to 96 % isolated yield.
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spelling pubmed-84569362021-09-27 Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions Fährmann, Jan Hilt, Gerhard Angew Chem Int Ed Engl Communications The acyl nitroso Diels–Alder reaction of 1,3‐dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro‐induced decomposition could be suppressed in favour of the 1,2‐oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3‐dienes and hydroxamic acids, giving up to 96 % isolated yield. John Wiley and Sons Inc. 2021-08-08 2021-09-06 /pmc/articles/PMC8456936/ /pubmed/34232547 http://dx.doi.org/10.1002/anie.202107148 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Fährmann, Jan
Hilt, Gerhard
Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title_full Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title_fullStr Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title_full_unstemmed Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title_short Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions
title_sort alternating current electrolysis as efficient tool for the direct electrochemical oxidation of hydroxamic acids for acyl nitroso diels–alder reactions
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456936/
https://www.ncbi.nlm.nih.gov/pubmed/34232547
http://dx.doi.org/10.1002/anie.202107148
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