Acid-catalyzed condensations of ninhydrin with aromatic compounds. Preparation of 2,2-diaryl-1,3-indanediones and 3-(diarylmethylene)isobenzofuranones

Authors
Klumpp, DA Fredrick, S Lau, S Jin, KK Bau, R Prakash, GKS Olah, GA
Citation
Da. Klumpp et al., Acid-catalyzed condensations of ninhydrin with aromatic compounds. Preparation of 2,2-diaryl-1,3-indanediones and 3-(diarylmethylene)isobenzofuranones, J ORG CHEM, 64(14), 1999, pp. 5152-5155
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
14
Year of publication
1999
Pages
5152 - 5155
Database
ISI
SICI code
0022-3263(19990709)64:14<5152:ACONWA>2.0.ZU;2-C
Abstract
Ninhydrin (1) reacts with aromatic compounds in acid solution to give conde nsation products. In H2SO4, 1 reacts with arenes to give 2,2-diaryl-1,3-ind anediones (2a-f). In superacidic triflic acid (CF3SO3H, TfOH), 1 reacts wit h arenes to give 3-(diarylmethylene)isobenzofuranones (3a-e). Products Ba-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.