A NEW SYNTHESIS OF SELENOUREAS AND SELENOTHIOCARBAMIC ESTERS FROM THIOUREAS

Selenoureas having either aliphatic or aromatic substituents were prepared by displacement of the thiomethyl moiety from S-methylthiopseudoureas by hydroselenide ion. The reaction, performed at pH 8-9, is general for all degrees of nitrogen substitution and gives yields in the range of 60-70%. At lower pH (ca. 5-6) displacement of an amino moiety by hydroselenide ion in several thiopseudoureas was observed to give selenothiocarbamates, a previously unreported class of compounds. © 1969, American Chemical Society. All rights reserved.