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Updated: Aug 23, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
N-Phenyl-N-[(E)-2-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)ethen-yl]aniline
Yuki Hatayama1, Kazuto Akagi1, Tsunehisa Okuno1
1Department of Systems Engineering, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan.
Abstract:
The title compound, C20H24BNO2, has a polarized π-system due to significant resonance between the N-C(H)=C(H)-B and ionic N+=C(H)-C(H)=B- canonical forms. The dihedral angles between the NC2B plane (r.m.s. deviation 0.0223 Å) and the C3N (r.m.s. deviation 0.0025 Å) and BCO2 (r.m.s. deviation 0.0044 Å) planes are 2.51 (12) and 3.09 (19)°, respectively. This indicates the lone pair of the nitro-gen atom and a vacant p orbital of the boron atom are conjugated with the central C=C bond. In comparison with the carbazole analogue [Hatayama & Okuno (2012 ▸). Acta Cryst. E68, o84], the C-N and C-B bonds are shorter. The results are well explained by the increase in the contribution of the N+=C(H)-C(H)=B- canonical form in the title compound.
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