Regioselective Synthesis of Aniline-Derived 1,3- and <i>C</i>_i-Symmetric 1,4-Diols from <i>trans</i>-1,4-Cyclohexadiene Dioxide

Abstract

trans-Diepoxide 1 is well-known to react with aliphatic amines and the azide ion to give exclusively the 1,3-diol products. However, we observed that by judicious choice of conditions, reaction with anilines can give predominantly the 1,3-diol (3) or the heretofore rarely seen Ci-symmetric 1,4-diol (4). Synthesis of an unsymmetrical 1,4-diol from two different anilines is also demonstrated. These studies demonstrate that an intramolecular anilino−NH hydrogen bond donor can direct Fürst−Plattner epoxide opening