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

J Org Chem

Department of Applied Chemistry (Japanese Association of Bio-intelligence for Well-being), Shibaura Institute of Technology, 3-7-5 Toyosu, Kohto-ku, Tokyo 135-8548, Japan.

Published: June 2022

-Methyl-2-methoxymethylanilines 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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http://dx.doi.org/10.1021/acs.joc.2c00845DOI Listing

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