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Reductive cleavage of the N–O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides

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Abstract

By treating with elemental sulfur in the presence of DABCO in DMSO, a variety of N-alkoxyamides were readily converted to amides in satisfactory to excellent yields via a metal-free reductive cleavage of the N–O bond. The mechanism of the reaction has been proposed based on the results of the control experiments, suggesting a process of cleavage of the N–O bond mediated by elemental sulfur, as well as the role played by DMSO in forming the amide in the product.

Graphical abstract: Reductive cleavage of the N–O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides

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Publication details

The article was received on 29 Sep 2018, accepted on 13 Dec 2018 and first published on 14 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01052H
Citation: Org. Chem. Front., 2019, Advance Article
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    Reductive cleavage of the N–O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides

    S. Wang, X. Zhao, D. Zhang-Negrerie and Y. Du, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01052H

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