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Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
Author(s) -
Wonneberger Peter,
König Nils,
Sárosi Menyhárt B.,
HeyHawkins Evamarie
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100898
Subject(s) - phosphole , lithium (medication) , protonation , chemistry , dimer , medicinal chemistry , hydride , ion , aluminum hydride , diene , reduction (mathematics) , computational chemistry , stereochemistry , organic chemistry , metal , mathematics , medicine , natural rubber , endocrinology , methoxide , geometry
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 2 H ‐phosphole dimer. Furthermore, 3 H ‐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.