Nucleophilic Carbenes of Pyrazoles Starting from Pseudo-Cross-Conjugated Mesomeric Betaines

Andreas      Schmidt; Tobias      Habeck

doi:10.2174/1570178053399903

Abstract

Pyrazolium-3-carboxylates, which belong to the class of pseudo-cross-conjugated heterocyclic mesomeric betaines, decarboxylate to give nucleophilic carbenes, which can be trapped as pyrazolium salts. An aldol addition, a Knoevenagel reaction, and a Cannizzaro-type reaction are presented, which are initiated by the strong basicity of the in situ generated pyrazol-3-ylidene.

Keywords: decarboxylation, 1,2-ylide, pyrazol-3-ylidenes, pyrazolium-3-carboxylates

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Letters in Organic Chemistry

Title: Nucleophilic Carbenes of Pyrazoles Starting from Pseudo-Cross-Conjugated Mesomeric Betaines

Volume: 2 Issue: 1

Author(s): Andreas Schmidt and Tobias Habeck

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Keywords: decarboxylation, 1,2-ylide, pyrazol-3-ylidenes, pyrazolium-3-carboxylates

Abstract: Pyrazolium-3-carboxylates, which belong to the class of pseudo-cross-conjugated heterocyclic mesomeric betaines, decarboxylate to give nucleophilic carbenes, which can be trapped as pyrazolium salts. An aldol addition, a Knoevenagel reaction, and a Cannizzaro-type reaction are presented, which are initiated by the strong basicity of the in situ generated pyrazol-3-ylidene.

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Schmidt Andreas and Habeck Tobias, Nucleophilic Carbenes of Pyrazoles Starting from Pseudo-Cross-Conjugated Mesomeric Betaines, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053399903