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Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene

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. Furth...

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Detalles Bibliográficos
Autores principales: Wonneberger, Peter, König, Nils, Sárosi, Menyhárt B., Hey‐Hawkins, Evamarie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251630/
https://www.ncbi.nlm.nih.gov/pubmed/33780580
http://dx.doi.org/10.1002/chem.202100898
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author Wonneberger, Peter
König, Nils
Sárosi, Menyhárt B.
Hey‐Hawkins, Evamarie
author_facet Wonneberger, Peter
König, Nils
Sárosi, Menyhárt B.
Hey‐Hawkins, Evamarie
author_sort Wonneberger, Peter
collection PubMed
description 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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spelling pubmed-82516302021-07-06 Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene Wonneberger, Peter König, Nils Sárosi, Menyhárt B. Hey‐Hawkins, Evamarie Chemistry Full Papers 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. John Wiley and Sons Inc. 2021-05-03 2021-05-20 /pmc/articles/PMC8251630/ /pubmed/33780580 http://dx.doi.org/10.1002/chem.202100898 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Full Papers
Wonneberger, Peter
König, Nils
Sárosi, Menyhárt B.
Hey‐Hawkins, Evamarie
Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title_full Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title_fullStr Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title_full_unstemmed Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title_short Reductive Rearrangement of a 1‐Phospha‐2‐azanorbornene
title_sort reductive rearrangement of a 1‐phospha‐2‐azanorbornene
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8251630/
https://www.ncbi.nlm.nih.gov/pubmed/33780580
http://dx.doi.org/10.1002/chem.202100898
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