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

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.