Superacid catalyzed ring-opening reactions involving 2-oxazolines and the role of superelectrophilic intermediates

DA Klumpp, R Rendy, A McElrea

Index: Klumpp, Douglas A.; Rendy, Rendy; McElrea, Aaron Tetrahedron Letters, 2004 , vol. 45, # 42 p. 7959 - 7961

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Citation Number: 20

Abstract

A variety of 2-oxazolines are found to react with arenes in superacidic triflic acid, CF3SO3H. It is proposed that the 2-oxazolines are protonated twice in triflic acid and the resulting intermediates undergo ring-opening reactions to produce reactive, dicationic species. These superelectrophiles are capable of reacting with benzene and o-dichlorobenzene in high yields by Friedel–Crafts type reactions.