Hydrogen-protected acenes

The first systematic study concerning the hydrogenation of acenes and acene quinones is presented. Phenyl substituted acenes and acene quinones are hydrogenated in excellent yield and with complete regioselectivity using HI-AcOH. The resulting H-protected acenes bear alternating aromatic and non-aromatic rings and are stable, soluble molecules that may be stored indefinitely and then deprotected to afford the parent acenes. In this manner, H-protected acenes have been utilized in the syntheses of several [60] fullerene-acene adducts. Buckminsterfullerene also hydrogenates in HI-AcOH yielding C-3 nu symmetric C60H18.