Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 37, Pages 20313-20317Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202107148
Keywords
alternating current; cycloaddition; Diels-Alder; electrochemistry; nitroso compounds
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The study presents the acyl nitroso Diels-Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids. By utilizing alternating current electrolysis and optimizing the reaction conditions through Design of Experiments, high purity products were obtained with yields up to 96%, without the need for further purification.
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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