Related Experiment Video
Updated: Jul 14, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
An epoxide intermediate in nucleophilic acylations by thiazolium precursors
1Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond, Virginia 23284, USA. sgronert@vcu.edu
Abstract:
Computational work at the MP2/6-31+G(d,p) level is used to explore the nucleophilic species derived from the fluoride activation of O-silylated thiazolium carbinols. These species recently have been shown by Scheidt to be useful acyl anion synthons, but the mechanism of their formation has been an open question. The data point to an unusual spiroepoxide intermediate that rearranges via acid/base chemistry to give the active nucleophile. The addition of the nucleophile to nitroethene is also examined.
More Related Videos
Related Concept Videos
Acid-Catalyzed Ring-Opening of Epoxides
Base-Catalyzed Ring-Opening of Epoxides
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...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

