ortho-DIQUATERNARY AROMATIC COMPOUNDS: I. THE SYNTHESIS OF ortho-DITERTIARYBUTYLBENZENE. SOME REACTIONS OF SIDE CHAIN SUBSTITUTED DERIVATIVES

1,1,4,4-Tetramethyltetralone (I) was converted by oxidative procedures into o-phenylene-diisobutyric acid (III). Hydride reduction of the dimethyl ester of III yielded β,β′-dihydroxy-o-di-t-butylbenzene (IV). The ditosylate of IV was converted by hydride reduction into o-di-t-butylbenzene (VI) (44%) together with rearrangement products. Ultraviolet spectral evidence indicated a slight distortion of the benzene ring in VI and its various side chain derivatives. Side reactions were encountered in the synthesis of III, which involved the conversion of this acid by periodate or lead tetraacetate oxidation into a lactone (X) and the anhydride (XI). A mechanism is postulated to account for the formation of X. The structures postulated for the various compounds were confirmed by n. m. r. spectral studies.