Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2004, Issue 16, Pages 3408-3411Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200400260
Keywords
nucleophilic aromatic substitution; zwitterions; Meisenheimer complexes; fluorescence spectroscopy; picric acid
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In this communication we present the first stable zwitterionic spirocyclic Meisenheimer compound based on an N --> N rearrangement in the reaction between picric acid and diisopropylcarbodiimide. The structure was confirmed by single-crystal X-ray diffraction. Furthermore, this compound exhibits interesting fluorescence properties (phi(f) = 0.4-0.5), not shared with a typical Meisenheimer complex, and a fluorescence lifetime (tau = 9.1 ns) in dichloromethane. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
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