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Elucidation of the structures of 3-alkylthio-, 3-benzylthio-, 2-arylthio- and 2-heteroarylthio-N1-(1,3-dimethylbutyl)-N4-phenyl-1,4-phenylenediamines by one- and two-dimensional NMR spectroscopy by Alan R. Katritzky; Novruz G. Akhmedov; Ashraf A. A. Abdel-Fattah; Mingyi Wang; Charles J. Rostek; Otto W. Maender is a Chemistry article available to read on EtoBox.
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## Abstract Nucleophilic addition of alkyl‐ and benzylthiols to benzoquinone diimine (**1**) gave the corresponding 3‐alkylthio‐ or 3‐benzylthio‐1,4‐phenylenediamines (**2**–**5**). However, addition of aryl‐ or heteroarylthiols to **1** formed 2‐arylthio‐ or 2‐heteroarylthio‐1,4‐phenylenediamines (**6**–**14**). The structures of **2**–**14**, obtained in 55–91% yields, were confirmed in CDCl~3~ or DMSO‐__d__~6~ solution using 1D (NOE difference, coupled ^13^C NMR spectra, APT and DEPT) and 2D NMR techniques [DQCOSY, NOESY, HETCOR and heteronuclear multiple bond coherence (HMBC)] that resulted in unambiguous proton and carbon NMR resonance assignments. The substituent‐induced ^13^C NMR chemical shift differences were calculated in **2**–**14** relative to carbon atoms in the model compound __N__^1^‐(1,3‐dimethylbutyl)‐__N__^4^‐phenyl‐1,4‐phenylenediamine (DMBPPD) (**15**) (a reduced form of benzoquinone diimine). Copyright © 2004 John Wiley & Sons, Ltd.
Who reads Elucidation of the structures of 3-alkylthio-, 3-benzylthio-, 2-arylthio- and 2-heteroarylthio-N1-(1,3-dimethylbutyl)-N4-phenyl-1,4-phenylenediamines by one- and two-dimensional NMR spectroscopy?
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- Author
- Alan R. Katritzky; Novruz G. Akhmedov; Ashraf A. A. Abdel-Fattah; Mingyi Wang; Charles J. Rostek; Otto W. Maender
- Publisher
- John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; John Wiley and Sons Ltd; Wiley (ISSN 0749-1581)
- Published
- 2004
- Language
- EN
- Field
- Chemistry (Physical Sciences)