A Case of Serendipity: Synthesis, Characterization, and Unique Chemistry of a Stable, Ring-Unsubstituted Aliphatic p-Quinone Methide.

We report the serendipitous synthesis of an indefinitely solution-stable ring-unsubstituted aliphatic p-quinone methide (p-QM) and detail its remarkable reaction chemistry through three archetypical chemical transformations: hydrogenation, hydride reduction, and nucleophilic addition. For example, the p-QM hydrogenates in a counterintuitive way; it resists all attempts at aromatization by catalytic reduction. Paradoxically, it does undergo aromatization/rearrangement upon reduction with LiAlH