Two’s Company, Six is a Crowded Triptycene

Significance

This work describes the truncated synthesis of hexaammonium triptycene - a valuable intermediate for the production of extended heterocyclic triptycene derivatives. The synthesis begins with a six-fold nitration of triptycene using fuming nitric acid to afford 18% of the hexa-nitro derivative. This compound is subsequently reduced using tin dichloride under acidic conditions to afford the title compound in quantitative yield. It is noteworthy that previous approaches require five steps and purification by column chromatography.