Thermal Rearrangement of the S-N Bond of Thiooxime Esters.

J Org Chem

Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.

Published: October 2024

AI Article Synopsis

  • The O-N bond in oxime esters allows for a variety of chemical reactions leading to different heterocyclic structures.
  • In contrast, the chemistry of thiooxime esters, which feature an S-N bond, has not been thoroughly investigated until now.
  • This study examines thiooxime esters' reactivity, revealing a specific fragmentation and rearrangement mechanism, marking the first look into the behavior of the S-N functional group.

Article Abstract

The labile O-N bond of oxime esters has enabled versatile access to many heterocyclic scaffolds. Alternatively, the analogous chemistry for thiooxime esters, which contain an S-N bond, has not been explored. Herein, we interrogate the reactivity of thiooxime esters and identify a homolytic fragmentation and rearrangement mechanism. This work provides the first exploration of the reactivity of this S-N functional group.

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Source
http://dx.doi.org/10.1021/acs.joc.4c01571DOI Listing

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