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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...

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Detalles Bibliográficos
Autores principales: Gubler, Joël, Chen, Peter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
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.
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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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