Separation of planar rotamers through intramolecular hydrogen bonding in polysubstituted 5-nitrosopyrimidines†‡
I. Císařová,M. Dračínský,Z. Janeba
Chemical Communications Pub Date : 10/08/2014 00:00:00 , DOI:10.1039/C4CC06978A
Abstract

While purifying new polysubstituted 5-nitrosopyrimidines, the unique separation of pairs of rotamers as chemical species, stabilized by a single intramolecular hydrogen bond and differing only in nitroso group orientation, was achieved. This interesting stereochemical phenomenon is compared to the well-known atropisomerism.

Graphical abstract: Separation of planar rotamers through intramolecular hydrogen bonding in polysubstituted 5-nitrosopyrimidines