The synthesis of new cyclic thioquinone derivatives

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 13C 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, 1H NMR, 13C 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. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:446–452, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20634