Superacid-Catalyzed Reactions of Cinnamic Acids and the Role of Superelectrophiles1

R Rendy, Y Zhang, A McElrea, A Gomez…

Index: Rendy, Rendy; Zhang, Yun; McElrea, Aaron; Gomez, Alma; Klumpp, Douglas A. Journal of Organic Chemistry, 2004 , vol. 69, # 7 p. 2340 - 2347

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Citation Number: 90

Abstract

The chemistry of cinnamic acids and related compounds has been studied. In superacid- catalyzed reactions with arenes, two competing reaction mechanisms are proposed. Both mechanisms involve the formation of dicationic intermediates (superelectrophiles), and the reactions can lead to either chalcone-type products or indanone products. The direct observation of a dicationic species (by low-temperature 13C NMR) is reported. We ...