Related Experiment Video
Updated: May 2, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
S-aroylthiooximes: a facile route to hydrogen sulfide releasing compounds with structure-dependent release kinetics
Jeffrey C Foster1, Chadwick R Powell, Scott C Radzinski
1Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
Abstract:
We report the facile preparation of a family of S-aroylthiooxime (SATO) H2S donors, which are synthesized via a click reaction analogous to oxime formation between S-aroylthiohydroxylamines (SATHAs) and aldehydes or ketones. Analysis of cysteine-triggered H2S release revealed structure-dependent release kinetics with half-lives from 8-82 min by substitution of the SATHA ring. The pseudo-first-order rate constants of substituted SATOs fit standard linear free energy relationships (ρ = 1.05), demonstrating a significant sensitivity to electronic effects.
More Related Videos
12:30Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
08:47Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
Published on: March 6, 2019
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Structure and Nomenclature of Thiols and Sulfides
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields...