Abstract
Condensation-type polythioamides have been prepared from bis(dithioester)s or bis(thioester)s with diamines. However, in contrast to the extensive study of polyamides, preparation and characterization of polythioamides have been limited. The Willgerodt–Kindler reaction is an important method for the synthesis of thioamides. In the reaction, aldehydes or ketones and amines in the presence of sulfur lead, via oxidation and rearrangement, to the terminal thioamides. Li et al. have recently reported synthesis of 1,4-dithiocarbonylpiperazines by this reaction. However, to our knowledge, there is no applied study of the Willgerodt–Kindler reaction to polymer synthesis. These observations prompted us to examine utility of the Willgerodt–Kindler reaction in an one-pot polycondensation of dialdehydes with diamines in the presence of sulfur to afford polythioamides. The polycondensation is expected to provide a convenient method for preparation of various polythioamides without the necessity for preparation of bis(dithioester)s or bis(thioester)s.
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