The Action of Hydrogen Sulfide on Aminoalkanethiosulfuric Acids (Bunte Salts) to Give Di-, Tri-, and Tetrasulfides

The reaction of hydrogen sulfide with several alkanethiosulfuric acids bearing amino functions has been studied. When primary and secondary aminoalkanethiosulfuric acids were treated with hydrogen sulfide, the product isolated in each case was the bis(aminoalkyl) disulfide thiosulfuric acid salt. 2-Aminoethaneseleno-sulfuric acid gave the corresponding diselenide XIV. Of the five tert-amino compounds treated with hydrogen sulfide, only 2-(dimethylamino)ethanethiosulfuric acid gave the expected disulfide. 2-Morpholinoethanethiosulfuric acid (III) gave the corresponding sulfenyl thiosulfate IV and trisulfide V. The other tert-aminoalkane-thiosulfuric acids produced tetrasulfides. Of these, di-n-heptylaminoethanethiosulfuric acid gave a tetra-sulfide which formed an unusually stable complex VII with six molecules of hydrogen sulfide. The synthesis of two unsaturated Bunte salts, 4-amino-2-butene-1-thiosulfuric acid (XVI) and 4-amino-2-butyne-1-thiosulfuric acid (XVII), has been achieved in a novel manner.