Title of article :
Structure of a push–pull olefin prepared by ynamine hydro­boration with a borandiol ester
Author/Authors :
Gubler, Joël Laboratorium für Organische Chemie - ETH Zürich, Zürich, Switzerland , Chen, Peter Laboratorium für Organische Chemie - ETH Zürich, Zürich, Switzerland
Pages :
14
From page :
1
To page :
14
Abstract :
N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenyl­ethen­yl]-N-(propan-2-yl)aniline, C23H22BNO2, 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.
Keywords :
crystal structure , hydro­boration , ynamine , push–pull olefin
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
Serial Year :
2020
Full Text URL :
Record number :
2624069
Link To Document :
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