Separation of the Enantiomers of 3,5-Dinitrophenyl Carbamates and 3,5-Dinitrophenyl Ureas

Abstract

Abstract The preparation of 3,5-dinitrophenyl carbamates and 3,5-dinitrophenyl ureas from chiral alcohols and amines and 3,5-dinitrobenzoyl azide is described. These ureas and carbamates have been observed to resolve on α-arylalkylamine based chiral stationary phases 1 and 2. A mechanism for the resolution of these carbamates and ureas is presented and compared to the resolution and mechanism thereof for the analogous series of 3,5-dinitrobenzamides on these phases.