Related Experiment Video
Updated: Aug 14, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Reaction of nitrones with silyl ketene acetals: a DFT study
Anne Milet1, Yves Gimbert, Andrew E Greene
1Chimie Recherche (LEDSS), Université Joseph Fourier, BP53, 38041 Grenoble, France.
Abstract:
Theoretical calculations at the DFT level indicate that the reaction of a nitrone with a silyl ketene acetal proceeds, contrary to previous suggestions, through a classical 1,3-dipolar cycloaddition, followed by a silyl group transfer step to give the open-chain product. Introduction of a diffuse basis set is necessary to describe properly nitrones. The influence of a Lewis acid has been studied.
More Related Videos
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Nitrosation of Enols
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Preparation of Nitriles
Nitriles to Ketones: Grignard Reaction
The mechanism begins with a nucleophilic attack by the Grignard reagent...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
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.