The Synthesis of New Thiosubstituted Compounds with Butadienyl and Butenynyl Groups

Abstract

Mono(thio)substituted butadiene 3a, tetrakis(thio)substituted butadiene 4b, and bis(thio)substituted butadiene 10j were synthesized from 1,1,3,3,4,4-hexachloro butene and aromatic thiols in dimethylformamide at room temperature in the presence of triethylamine. Thiosubstituted butenyne compounds 5c, 6a, 7a,h, and 11i and butadiene compounds 3f,g, 4d, 8g, 9d, and 10i were synthesized from 1,1,3,3,4,4-hexachloro butene and different thiols in EtOH with NaOH solution. The thiosubstituted butadienes 13e and 14f were obtained from the reactions of 2H-1,1,3,4,-tetrachloro-4-bromo-butadiene and thiols in EtOH/H2O solution of NaOH. The structures of the new compounds were determined by microanalysis, FT-IR, UV/Vis, 1H NMR, 13C NMR, 19F NMR, MS, and fluorescence spectrophotometry. GRAPHICAL ABSTRACT[image omitted].