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Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester
N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenylethenyl]-N-(propan-2-yl)aniline, C(23)H(22)BNO(2), contains a C=C bond that is conjugated with a donor and an acceptor group. An analysis that included similar push–pull olefins revealed that bond lengths in their B—C=C—N core units correlate with t...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7199258/ https://www.ncbi.nlm.nih.gov/pubmed/32431937 http://dx.doi.org/10.1107/S2056989020005289 |
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author | Gubler, Joël Chen, Peter |
author_facet | Gubler, Joël Chen, Peter |
author_sort | Gubler, Joël |
collection | PubMed |
description | N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenylethenyl]-N-(propan-2-yl)aniline, C(23)H(22)BNO(2), contains a C=C bond that is conjugated with a donor and an acceptor group. An analysis that included similar push–pull olefins revealed that bond lengths in their B—C=C—N core units correlate with the perceived acceptor and donor strength of the groups. The two phenyl groups in the molecule are rotated with respect to the plane that contains the BCCN atoms, and are close enough for significant π-stacking. Definite characterization of the title compound demonstrates, for the first time in a reliable way, that hydroboration of ynamines with borandiol esters is feasible. Compared to olefin hydroboration with borane, the ynamine substrate is activated enough to undergo reaction with the less active hydroboration reagent catecholborane. |
format | Online Article Text |
id | pubmed-7199258 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-71992582020-05-19 Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester Gubler, Joël Chen, Peter Acta Crystallogr E Crystallogr Commun Research Communications N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenylethenyl]-N-(propan-2-yl)aniline, C(23)H(22)BNO(2), contains a C=C bond that is conjugated with a donor and an acceptor group. An analysis that included similar push–pull olefins revealed that bond lengths in their B—C=C—N core units correlate with the perceived acceptor and donor strength of the groups. The two phenyl groups in the molecule are rotated with respect to the plane that contains the BCCN atoms, and are close enough for significant π-stacking. Definite characterization of the title compound demonstrates, for the first time in a reliable way, that hydroboration of ynamines with borandiol esters is feasible. Compared to olefin hydroboration with borane, the ynamine substrate is activated enough to undergo reaction with the less active hydroboration reagent catecholborane. International Union of Crystallography 2020-04-21 /pmc/articles/PMC7199258/ /pubmed/32431937 http://dx.doi.org/10.1107/S2056989020005289 Text en © Gubler and Chen 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Gubler, Joël Chen, Peter Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title | Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title_full | Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title_fullStr | Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title_full_unstemmed | Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title_short | Structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
title_sort | structure of a push–pull olefin prepared by ynamine hydroboration with a borandiol ester |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7199258/ https://www.ncbi.nlm.nih.gov/pubmed/32431937 http://dx.doi.org/10.1107/S2056989020005289 |
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