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The thioketo and thioenol tautomers of thioacetone have been separated by gas chromatography and characterized by infrared and NMR spectra at low temperatures. The pure thioketo tautomer polymerizes rapidly at room temperature, but the thioenol tautomer does not. At room temperature, the thioenol gradually disappears, probably by tautomerization to the reactive thioketo form, which then polymerizes. Attempts to copolymerize thioacetone with vinyl and diene monomers were not successful.
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Lipscomb et al. (1970) studied this question.
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