2012European Journal of Organic ChemistryRequires access

Recent Highlights in Ketenimine Chemistry

Mateo Alajarı́n, Marta Marín‐Luna, Ángel Vidal

Open publisher page 111 citations

Abstract

Abstract Selected recent developments in the chemistry of ketenimines are presented, demonstrating that heterocumulenes of this class are versatile reactive intermediates in the synthesis of nitrogenated heterocycles. This microreview includes examples of intramolecular nucleophilic and radical additions, biradical cyclizations, 4π‐ and 6π‐electrocyclic ring closures, [2+2], [3+2] and [4+2] cycloadditions, ketenimine‐to‐nitrile rearrangements and 1,3‐X, 1,5‐X and 1,5‐H shifts.

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What this paper is about

Abstract Selected recent developments in the chemistry of ketenimines are presented, demonstrating that heterocumulenes of this class are versatile reactive intermediates in the synthesis of nitrogenated heterocycles. This microreview includes examples of intramolecular nucleophilic and radical additions, biradical cyclizations, 4π‐ and 6π‐electrocyclic ring closures, [2+2], [3+2] and [4+2] cycloadditions, ketenimine‐to‐nitrile rearrangements and 1,3‐X, 1,5‐X and 1,5‐H shifts.

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Available abstract

Abstract Selected recent developments in the chemistry of ketenimines are presented, demonstrating that heterocumulenes of this class are versatile reactive intermediates in the synthesis of nitrogenated heterocycles. This microreview includes examples of intramolecular nucleophilic and radical additions, biradical cyclizations, 4π‐ and 6π‐electrocyclic ring closures, [2+2], [3+2] and [4+2] cycloadditions, ketenimine‐to‐nitrile rearrangements and 1,3‐X, 1,5‐X and 1,5‐H shifts.

Key concepts: Ketenimine, Chemistry, Intramolecular force, Ring (chemistry), Nucleophile, Nitrile, Electrocyclic reaction, Nucleophilic addition

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