Acid-Catalyzed Condensations of Ninhydrin with Aromatic Compounds. Preparation of 2, 2-Diaryl-1, 3-indanediones and 3-(Diarylmethylene) isobenzofuranones1

…, S Lau, KK Jin, R Bau, GK Surya Prakash…

Index: Klumpp, Douglas A.; Fredrick, Shyla; Lau, Siufu; Jin, Kevin K.; Bau, Robert; Surya Prakash; Olah, George A. Journal of Organic Chemistry, 1999 , vol. 64, # 14 p. 5152 - 5155

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Citation Number: 35

Abstract

Ninhydrin (1) reacts with aromatic compounds in acid solution to give condensation products. In H2SO4, 1 reacts with arenes to give 2, 2-diaryl-1, 3-indanediones (2a-f). In superacidic triflic acid (CF3SO3H, TfOH), 1 reacts with arenes to give 3-(diarylmethylene) isobenzofuranones (3a-e). Products 3a-e are proposed to have formed by a condensation and rearrangement involving dicationic intermediates. Benzo [f] ninhydrin also reacts with ...