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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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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. |
format | Online Article Text |
id | pubmed-8456936 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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