Chromatographically separable rotamers of an unhindered amide

• Verfasst von: Geffe, Mario [VerfasserIn]
• Verfasst von: Andernach, Lars [VerfasserIn]
• Verfasst von: Trapp, Oliver [VerfasserIn]
• Verfasst von: Opatz, Till [VerfasserIn]
• Titel: Chromatographically separable rotamers of an unhindered amide
• Verf.angabe: Mario Geffe, Lars Andernach, Oliver Trapp and Till Opatz
• E-Jahr: 2014
• Jahr: 21 March 2014
• Umfang: 6 S.
• Fussnoten: Gesehen am 29.09.2020
• Titel Quelle: Enthalten in: Beilstein journal of organic chemistry
• Ort Quelle: Frankfurt, Main : Beilstein-Institut zur Förderung der Chemischen Wissenschaften, 2005
• Jahr Quelle: 2014
• Band/Heft Quelle: 10(2014), Seite 701-706
• ISSN Quelle: 1860-5397
• DOI: doi:10.3762/bjoc.10.63
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 173395743X

Abstract

Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were compared to each other as well as to results obtained by DFT calculations.