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Synthesis 1993; 1993(11): 1077-1079
DOI: 10.1055/s-1993-26001
short paper
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Superelectrophilic Tscherniac Amidomethylation of Aromatics with N-Hydroxymethylphthalimide in Trifluoromethanesulfonic Acid

George A. Olah* , Qi Wang, Graham Sandford, Alexandros B. Oxyzoglou, G. K. Surya Prakash
  • *Donald P. and Katherine B. Loker Hydrocarbon Institute, University of Southern California, Los Angeles, California 90089-1661, USA
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Publication Date:
29 April 2002 (online)

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N-Hydroxymethylphthalimide in trifluoromethanesulfonic acid (triflic acid) reacts readily at room temperature with benzene, halo-, polyhalo- and halonitrobenzenes to give high yields of the corresponding α-amidomethylated products. The scope of the α-amidomethylation reaction is substantially extended by the studied system, which is considered to involve diprotonated N-hydroxymethylphthalimide as the de facto superelectrophilic reagent.