Related Experiment Video
Updated: Mar 17, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Synthesis, Structure, and Unusual Reactivity of a Stable 3-(Oxazolidin-2-ylidene)thiophen-2-one
R Alan Aitken1, Andrew D Harper1, Alexandra M Z Slawin1
1EaStCHEM School of Chemistry, University of St Andrews , North Haugh, St Andrews, Fife KY16 9ST, U.K.
Abstract:
Treatment of 2- and 3-thienyloxazolines with butyllithium and bis(trimethylsilyl) peroxide results in ring hydroxylation to give products that exist mainly as the oxazolidinylidenethiophenones. The 3-oxazolidinylidenethiophen-2-one is a rare example of a stable heterocyclic o-quinone methide analogue that shows a varied pattern of reactivity, including both C- and O-alkylation, Michael addition via C-5 to an acetylenic ester, tetrachlorobenzannulation across positions 4 and 5, and formation of a hexacyclic fused-ring product with N-phenyltriazolinedione. Crystal structures of the products are dominated by inter- and intramolecular NH to CO hydrogen bonding.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Acid-Catalyzed Ring-Opening of Epoxides
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Radical Reactivity: Overview
![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)
