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Updated: Jun 5, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Phosphirane-Enabled Synthesis of Aromatic 1H-1,2-Azaphospholes and Phosphinines
Chenyong Xu1, Zhenyun Dai1, Shaopeng Kang1
1College of Chemistry, International Phosphorus Laboratory, Zhengzhou University, Zhengzhou 450001, P. R. China.
Abstract:
Aromatic heteroarenes are essential components of numerous valuable molecules. Herein we present a simple and effective route to access aromatic 1H-1,2-azaphospholes and phosphinines. This method utilizes the ring tension of phosphiranes to convert simple β-chloroethylphosphane and alkynyl imines into these valuable compounds. The nucleophilic addition of the phosphiranide complex to alkynyl imines results in phosphiranes 3, which transform into 1H-1,2-azaphospholes under mild conditions. The skeletal editing of 1,2-azaphospholes into phosphinine derivatives was accomplished through a cascade process involving a [4 + 2] cycloaddition and the elimination of a nitrogen moiety.
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