A “Green” Route to Perylene Dyes: Direct Coupling Reactions of 1,8-Naphthalimide and Related Compounds under Mild Conditions Using a “New” Base Complex Reagent, t-BuOK/DBN
- 12 December 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (1) , 94-98
- https://doi.org/10.1021/jo0010835
Abstract
The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 degrees C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with > 95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.Keywords
This publication has 23 references indexed in Scilit:
- 3,4:9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptorsTetrahedron Letters, 1999
- Peryleneimidazoloimides: Highly Fluorescent and Stable Replacements of TerryleneAngewandte Chemie International Edition in English, 1999
- Liquid Crystalline Coronene Derivatives with Extraordinary Fluorescence PropertiesAngewandte Chemie International Edition in English, 1998
- Intense Dyes through Chromophore-Chromophore Interactions: Bi- and Trichromophoric Perylene-3,4:9,10-bis(dicarboximide)sAngewandte Chemie International Edition in English, 1998
- Benzoylperylenedicarboximides: Functional dyes with attractive optical and electronic propertiesTetrahedron, 1997
- Synthesis of Soluble Perylenebisamidine Derivatives. Novel Long-Wavelength Absorbing and Fluorescent DyesChemistry of Materials, 1997
- Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivativesCanadian Journal of Chemistry, 1995
- Cyclic Carboxylic Imide Structures as Structure Elements of High Stability. Novel Developments in Perylene Dye ChemistryHETEROCYCLES, 1995
- Unimetal super basesChemical Reviews, 1993
- Nuclear substitution by anions and self-union in 1 : 8-naphthalimide and its N-methyl derivativeJournal of the Chemical Society, 1954