Rotational Behavior of N‑(5-Substituted-pyrimidin-2-yl)anilines: Relayed Electronic Effect in Two N–Ar Bond Rotations

Daiki Homma,Shuhei Taketani,Takeshi Shirai,Elsa Caytan,Christian Roussel,José Elguero,Ibon Alkorta,Osamu Kitagawa

The Journal of Organic Chemistry（2022）

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摘要

N-Methyl-2-methoxymethylanilines 1 bearing various 5-substituted-pyrimidin-2-yl groups were prepared, and their rotational behaviors were explored in detail. It was revealed that the rotational barriers around two N–Ar bonds increase in proportion to the electron-withdrawing ability of substituents X at the 5-position.

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