Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 46, Pages 6175-6179Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202101017
Keywords
sigma Adducts; Microscopic reversibility; Nitroarenes; Nucleophilic substitution; Radical ions
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Analysis of the effects of various parameters on reactions of C, N, and O nucleophiles with nitroarenes reveals two major pathways: direct addition leading to substitution of hydrogen or halogens, and single electron transfer (SET) leading to other processes. In some rare cases, paramagnetic species generated by SET can combine, resulting in substitution.
Analysis of effects of various parameters on reactions of C, N and O nucleophiles with nitroarenes leads to the conclusion that there are two different major pathways: direct addition leading to substitution of hydrogen or halogens and single electron transfer (SET), leading to other processes. In some, rather rare cases, paramagnetic species generated by SET can combine, resulting in substitution.
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