Structural diversity of interaction products of mucochloric acid and its derivatives with 1,2-ethanedithiol

Abstract

The synthesis and characterization of previously unknown sulfur-containing products from the reaction of mucochloric acid (3,4-dichloro-5-hydroxy-2(5H)- furanone) and its 5-alkoxy derivatives with 1,2-ethanedithiol is reported. Under basic and acidic conditions both SH-groups of the reagent show nucleophilic activity, leading to the formation of substitution products of different structural types. Novel fused (7-hydroxy-2,3-dihydro[1,4]dithiino[2,3-c]furan- 5(7H)-one) and spiro (9-chloro-6-methoxy-7-oxa-1,4-dithiaspiro[4.4]nonan-8-one) bicyclic compounds, as well as various bis-thioethers have been obtained and characterized by NMR spectroscopy and single crystal X-ray diffraction. © 2010 Elsevier Ltd. All rights reserved.