Related Experiment Video
Updated: Feb 5, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Electrochemical Activation of α-Carbonyl Alkoxyamines for Direct Nucleophilic Substitution
John Putziger1, Elya Kandahari1, Song Lin1
1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Abstract:
The reactivity and synthetic utility of TEMPO-derived alkoxyamines as functional handles remains insufficiently explored. This report interrogates the factors governing the stereospecific substitution of electroactivated TEMPO-derived α-carbonyl alkoxyamines. Concurrent with direct electrolysis, electroanalytical studies and theoretical calculations provided a complementary platform by which one could predict the efficacy for substrates to undergo desired substitution using benzoic acid or N-sulfonyl carbamate nucleophiles.
More Related Videos
Related Concept Videos
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Nucleophilic Addition to the Carbonyl Group: General Mechanism
A stronger nucleophile can directly attack the electrophilic center, the carbonyl carbon. The HOMO orbital of the nucleophile interacts with the LUMO (π* antibonding) orbital present on the carbonyl carbon. This interaction breaks the π bond and shifts the π...
Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Nucleophilic Aromatic Substitution: Elimination–Addition

