ChemInform Abstract: SYNTHETIC METHODS AND REACTIONS PART 11, A CONVENIENT DIRECT PREPARATION OF 1,3,5‐TRINITROBENZENE FROM M‐DINITROBENZENE BY NITRATION WITH NITRONIUM TETRAFLUOROBORATE IN FLUOROSULFURIC ACID SOLUTION

Superelectrophilic Solvation

“…2,6 Carboxylic acids can also form a variety of distonic superelectrophilic intermediates by protonation of the carboxylic acid group and ionization of adjacent functional groups. R-Keto acids generate reactive electrophilic (45,46) species capable of condensing with arenes in high yields (eqs 10 and 11). 35 Benzilic acid gives fluorine-9carboxylic acid almost quantitatively (eq 12) in excess H 2 -SO 4 or AlCl 3 via dication 47.…”

“…In 1974, the first observation of the enhanced electrophilic reactivity of nitronium salts (65) in superacid was reported, 45 and the protosolvation of the nitronium ion was later suggested (66, NO 2 H 2+ , Scheme 10). 3 More recently, a mixture of nitric acid and triflatoboric acid (2 CF 3 SO 3 H-(CF 3 SO 3 ) 3 B; H o ) -20.5) 46 was shown to nitrate deactivated arenes in high yields, and the reactivity of this system was attributed to the formed protonitronium dication (NO 2 H 2+ ).…”