ORGANIC SULFUR CHEMISTRY .36. CYCLIC TRISULFIDES BY ALKOXIDE DECOMPOSITION OF BIS-(SULFENYL) THIOCARBONATES

A series of bis(sulfenylated) thiocarbonates (CH302SS(CH2)nSSCO2CH3) was prepared and treated with potassium ferf-butoxide in an effort to synthesize monocyclic trisulfides. In all cases (n = 2-10), polymeric material was obtained, and no target compounds were isolated. For n = 6, 7, 8, 10, cyclic bis(trisulfides) (dimers) were formed in moderate yield. Structural evidence for these macrocycles derives largely from MS, 13C NMR, and osmometric molecular weight determinations. Copyright © 1979, American Chemical Society. All rights reserved.