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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

✍ Scribed by Alan R. Katritzky; Novruz G. Akhmedov; Ashraf A. A. Abdel-Fattah; Mingyi Wang; Charles J. Rostek; Otto W. Maender

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
204 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

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.

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