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CAAC‐Based Thiele and Schlenk Hydrocarbons
Diradicals have been of tremendous interest for over a century ever since the first reports of p‐ and m‐phenylene‐bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele's hydrocarbon, a...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187164/ https://www.ncbi.nlm.nih.gov/pubmed/31960562 http://dx.doi.org/10.1002/anie.201915802 |
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author | Maiti, Avijit Stubbe, Jessica Neuman, Nicolás I. Kalita, Pankaj Duari, Prakash Schulzke, Carola Chandrasekhar, Vadapalli Sarkar, Biprajit Jana, Anukul |
author_facet | Maiti, Avijit Stubbe, Jessica Neuman, Nicolás I. Kalita, Pankaj Duari, Prakash Schulzke, Carola Chandrasekhar, Vadapalli Sarkar, Biprajit Jana, Anukul |
author_sort | Maiti, Avijit |
collection | PubMed |
description | Diradicals have been of tremendous interest for over a century ever since the first reports of p‐ and m‐phenylene‐bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele's hydrocarbon, a Kekulé diradical, and Schlenk's hydrocarbon, a non‐Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele's hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk's hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head‐to‐tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox‐active organic compounds. |
format | Online Article Text |
id | pubmed-7187164 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-71871642020-04-28 CAAC‐Based Thiele and Schlenk Hydrocarbons Maiti, Avijit Stubbe, Jessica Neuman, Nicolás I. Kalita, Pankaj Duari, Prakash Schulzke, Carola Chandrasekhar, Vadapalli Sarkar, Biprajit Jana, Anukul Angew Chem Int Ed Engl Communications Diradicals have been of tremendous interest for over a century ever since the first reports of p‐ and m‐phenylene‐bridged diphenylmethylradicals in 1904 by Thiele and 1915 by Schlenk. Reported here are the first examples of cyclic(alkyl)(amino)carbene (CAAC) analogues of Thiele's hydrocarbon, a Kekulé diradical, and Schlenk's hydrocarbon, a non‐Kekulé diradical, without using CAAC as a precursor. The CAAC analogue of Thiele's hydrocarbon has a singlet ground state, whereas the CAAC analogue of Schlenk's hydrocarbon contains two unpaired electrons. The latter forms a dimer, by an intermolecular double head‐to‐tail dimerization. This straightforward synthetic methodology is modular and can be extended for the generation of redox‐active organic compounds. John Wiley and Sons Inc. 2020-03-06 2020-04-20 /pmc/articles/PMC7187164/ /pubmed/31960562 http://dx.doi.org/10.1002/anie.201915802 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Maiti, Avijit Stubbe, Jessica Neuman, Nicolás I. Kalita, Pankaj Duari, Prakash Schulzke, Carola Chandrasekhar, Vadapalli Sarkar, Biprajit Jana, Anukul CAAC‐Based Thiele and Schlenk Hydrocarbons |
title | CAAC‐Based Thiele and Schlenk Hydrocarbons |
title_full | CAAC‐Based Thiele and Schlenk Hydrocarbons |
title_fullStr | CAAC‐Based Thiele and Schlenk Hydrocarbons |
title_full_unstemmed | CAAC‐Based Thiele and Schlenk Hydrocarbons |
title_short | CAAC‐Based Thiele and Schlenk Hydrocarbons |
title_sort | caac‐based thiele and schlenk hydrocarbons |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7187164/ https://www.ncbi.nlm.nih.gov/pubmed/31960562 http://dx.doi.org/10.1002/anie.201915802 |
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