Hydrogen transfer reactions in strongly acid media

The reactions of cations derived from acid (H2SO4, HF, or HSO3F) solns. of pentamethylbenzyl chloride (I), pentamethylbenzyl-amine (II), chloromethyldurene (III), bis(chloromethyl)durene (IV), bis(chloromethyl)prehnitene (V), and tetracene (VI) with H, alkanes, and aromatic compds. were studied spectroscopically. The cation from I reacted with an alkane to give protonated hexamethylbenzene while with 9,10-dihydroanthracene, the formation of the mesoanthracenium ion and protonated hexamethylbenzene is confined by uv spectra. The ion derived from II was the [(ammoniomethyl)tetramethylphenyl]methylium which did not react with alkanes. III, IV, and V were sol. only in HSO3F, and addn. of isooctane to the [(chloromethyl)tetramethylphenyl]methylium derived from IV or V caused a color change from bluish violet to yellow. Reaction of alkanes with the dipos. ion of VI in H2SO4 was high, owing to rapid hydride ion extn. from the alkane. [on SciFinder (R)