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

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)8118-8125
Number of pages8
JournalJournal of Organic Chemistry
Volume87
Issue number12
DOIs
Publication statusPublished - 2022 Jun 17

ASJC Scopus subject areas

  • Organic Chemistry

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