Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs

Reactions of PAr(3)/B(C(6)F(5))(3) (Ar=o‐Tol, Mes, Ph) FLPs with diethyl azodicarboxylate (DEAD) afford the corresponding FLP addition products 1–3 in which P−N and B−O linkages are formed. In contrast, the reaction of BPh(3), PPh(3) and DEAD gave product 4 where P−N and N−B linkages were confirmed....

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Autores principales: Mandal, Dipendu, Chen, Ting, Qu, Zheng‐Wang, Grimme, Stefan, Stephan, Douglas W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9796924/
https://www.ncbi.nlm.nih.gov/pubmed/35670767
http://dx.doi.org/10.1002/chem.202201701
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author Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
author_facet Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
author_sort Mandal, Dipendu
collection PubMed
description Reactions of PAr(3)/B(C(6)F(5))(3) (Ar=o‐Tol, Mes, Ph) FLPs with diethyl azodicarboxylate (DEAD) afford the corresponding FLP addition products 1–3 in which P−N and B−O linkages are formed. In contrast, the reaction of BPh(3), PPh(3) and DEAD gave product 4 where P−N and N−B linkages were confirmed. In all cases, other binding modes were computed to be both higher in energy and readily distinguishable by (31)P and (11)B NMR parameters. These data illustrate the influence of steric demands and electronic structures on the nature of the products of FLP reactions with DEAD.
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spelling pubmed-97969242023-01-04 Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs Mandal, Dipendu Chen, Ting Qu, Zheng‐Wang Grimme, Stefan Stephan, Douglas W. Chemistry Research Articles Reactions of PAr(3)/B(C(6)F(5))(3) (Ar=o‐Tol, Mes, Ph) FLPs with diethyl azodicarboxylate (DEAD) afford the corresponding FLP addition products 1–3 in which P−N and B−O linkages are formed. In contrast, the reaction of BPh(3), PPh(3) and DEAD gave product 4 where P−N and N−B linkages were confirmed. In all cases, other binding modes were computed to be both higher in energy and readily distinguishable by (31)P and (11)B NMR parameters. These data illustrate the influence of steric demands and electronic structures on the nature of the products of FLP reactions with DEAD. John Wiley and Sons Inc. 2022-07-27 2022-09-22 /pmc/articles/PMC9796924/ /pubmed/35670767 http://dx.doi.org/10.1002/chem.202201701 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Mandal, Dipendu
Chen, Ting
Qu, Zheng‐Wang
Grimme, Stefan
Stephan, Douglas W.
Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title_full Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title_fullStr Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title_full_unstemmed Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title_short Reactions of Diethylazo‐Dicarboxylate with Frustrated Lewis Pairs
title_sort reactions of diethylazo‐dicarboxylate with frustrated lewis pairs
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9796924/
https://www.ncbi.nlm.nih.gov/pubmed/35670767
http://dx.doi.org/10.1002/chem.202201701
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