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