Reactions of 3-phenyloxetane and 7-oxabicyclo[2.2.1]heptane with dinitrogen pentoxide in dichloromethane

Abstract

3-Phenyloxetane reacts initially almost entirely by ortho and para aromatic nitration. This is followed by oxetane ring-opening to give the corresponding 2-arylpropane-1,3-diol dinitrates. The oxetane ring-opening reactions, and the reaction of 7-oxabicyclo[2.2.1]heptane to give exclusively trans-cyclohexane-1,4-diol dinitrate, are approximately second order in dinitrogen pentoxide and have highly negative entropies of activation.