Relayed Proton Brake in N-Pyridyl-2-iso-propylaniline Derivative: Two Brakes with One Proton

Gaku Furukawa, Takeshi Shirai, Yuki Homma, Elsa Caytan, Nicolas Vanthuyne, Daniel Farran, Christian Roussel, Osamu Kitagawa

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

The addition of methanesulfonic acid to N-(2,6-dimethylpyridin-4-yl)-N-methyl-2-iso-propylaniline led to the selective protonation of the pyridine nitrogen atom, resulting in a significant deceleration of the rotation rates around both N-pyridyl and N-(i-Pr)phenyl bonds through a relayed brake mechanism.

Original languageEnglish
Pages (from-to)5109-5113
Number of pages5
JournalJournal of Organic Chemistry
Volume85
Issue number7
DOIs
Publication statusPublished - 2020 Apr 3

ASJC Scopus subject areas

  • Organic Chemistry

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