The Synthesis of New Cyclic Thioquinone Derivatives

Abstract

New bis(thio)substituted, S-,O-substituted, and S-,S-substituted benzoquinone compounds were synthesized from the reaction of p-chloranil (1) with S-,O-substituted thiols, dithiols, and monothiols. The (13)C NMR spectra and the IR spectra of heterocyclic compounds 3, 4 and 7, 8 showed different behavior; that of 3, 7 showed a carbon signal and a >C=O group band for the carbonyl group and that of 4, 8 showed two carbon signals and split bands for the carbonyl group. The structures of the novel compounds were characterized by microanalysis, FT-IR, (1)H NMR, (13)C NMR, MS, and UV-vis spectroscopy. The crystal structure of 2,3,5,6-tetrakis(4-fluorobenzylthio)cyclohexa-2,5-diene-1,4-dione (15) was determined by the X-ray diffraction method. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:446-452, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20634