Oxidation of Chiral 2(5H)-Furanone Bis-Thioethers to Disulfoxides

Novel disulfinyl derivatives based on 3,4-dichloro-2(5H)-furanone, aliphatic dithiols, and monoterpene alcohols were synthesized. Chiral bis-thioethers in the molecules of which dithiol fragment links two five-membered cycles at C4 atoms obtained reactions 5(S)-(l-menthyloxy)- 5(S)-(l-bornyloxy)-2(5H)-furanones with ethane-1,2-dithiol propane-1,3-dithiol acetone basic medium. The action an excess m-chloroperoxybenzoic acid (2.0–3.2 equiv.) led to formation corresponding mono- disulfoxides bearing l-menthol or l-borneol fragments 5th position lactone ring. methods column chromatography fractional recrystallization used for isolation individual products. structure synthesized heterocycles was proved by IR NMR spectroscopy, their composition confirmed high-resolution mass spectrometry. molecular three characterized X-ray diffraction analysis.