Reductive cleavage of the N–O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides
Literature Information
Publication Date
2018-12-14
DOI
10.1039/C8QO01052H
Impact Factor
5.281
Authors
Senlin Wang, Xue Zhao, Daisy Zhang-Negrerie
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
2-Methyl-2-propanyl 4-iodo-1-piperidinecarboxylate
CAS Number:
301673-14-3
Molecular Formula:
C10H18INO2
![N-[(E)-Phenylmethylene]benzenesulfonamide structure](https://static.chemtradehub.com/structs/139/13909-34-7-8167.webp "N-[(E)-Phenylmethylene]benzenesulfonamide structure")
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