ETHYLENE THIONOCATBONATE AND 1,3-OXATHIOLANE-2-THIONE

Synthesis and reactions of the title compounds are reported. These compounds are isomerized to thiol- and dithiolcarbonates by halide ions. Alkylation with alkyl halides gives unstable intermediates which rearrange to β-haloethyl thiol- and dithiolcarbonates. Acids induce polymerization to polythiol and polydithiolcarbonates. Both 1 and 2 give ethylene when treated with triphenylphosphine. Nmr and ir spectral comparisons of the six possible ethylene carbonates with sulfur substituted for oxygen are tabulated. © 1969, American Chemical Society. All rights reserved.