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Updated: Nov 11, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Reductive Rearrangement of a 1-Phospha-2-azanorbornene
Peter Wonneberger1, Nils König1, Menyhárt B Sárosi1
1Leipzig University, Faculty of Chemistry and Mineralogy, Institute of Inorganic Chemistry, Johannisallee 29, 04103, Leipzig, Germany.
Abstract:
The reduction of the 1-phospha-2-azanorbornene derivate endo-1 with lithium aluminium hydride leads to an unprecedented 1-phosphabicyclo[3.2.1]octa-2,5-diene, while a phospholide anion is formed with lithium. The latter can be protonated resulting in formation of an unusual 2H-phosphole dimer. Furthermore, 3H-phospholes, previously assumed to have no synthetic relevance as intermediates, were proposed to act as dienophile in the dimerisation of 3,4-dimethyl-1-phenylphosphole at elevated temperatures based on theoretical calculations.
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