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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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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. |
format | Online Article Text |
id | pubmed-8251630 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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