Treatment of compound 1 with benzene in triflic acid
Chapter 19, Problem 19.91(choose chapter or problem)
Treatment of compound 1 with benzene in triflic acid (CF3SO3H) affords ammonium ion 3 (J. Org. Chem. 1999, 64, 67026705). Triflic acid is an extremely strong acid (pKa = -14), even more acidic than sulfuric acid; under these conditions, the transformation is believed to proceed via intermediate 2, a highly electrophilic dication. Draw a complete mechanism for the conversion of 1 to 3. N O N O H H N C6H6 F3C S O O OH 1 2 3 H ! ! !
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