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. 1999 Jul 9;64(14):5152-5155.
doi: 10.1021/jo990197h.

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

Douglas A Klumpp  1 , Shyla Fredrick  1 , Siufu Lau  1 , Kevin K Jin  1 , Robert Bau  1 , G K Surya Prakash  1 , George A Olah  1
Affiliations

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

Douglas A Klumpp et al. J Org Chem. .

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 C6H6 in H2SO4 to give a similar condensation product.

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