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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 10
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Original Articles

A Study on the Friedel-Crafts Type Reaction of Ninhydrin with Arenes

, , &
Pages 1865-1870 | Received 11 Nov 1997, Published online: 20 Aug 2006
 

Abstract

The reactions of ninhydrin (1, 1,2,3-indantrione) with arenes in the presence of concentrated sulfuric acid afforded mono- or di-substituted ninhydrin derivatives at the 2-position in reasonable yields.

Notes

2,3-Dihydroxy-2,3-diphenyl-1-indanone: mp 175–177 °C; 1H NMR (CDCl3) δ 3.95 (s, 1H), 4.38 (s, 1H), 6.75–8.10 (m, 14H); 13C NMR (CDCl3) δ 82.96, 85.83, 123.92, 126.80, 126.91, 127.16, 127.20, 127.26, 127.42, 127.51, 130.13, 135.68, 136.41, 138.59, 140.14, 155.16, 204.11; Mass (20 eV) m/z (rel intensity) 77 (17), 105 (100), 132 (43), 133 (65), 209 (30), 210 (49), 221 (51), 298 (100), 299 (100), 316 (M+, 8)

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