REACTIVITY OF THIOHYDROXYLAMINES TOWARD B ENZOIC ANHYDRIDE AND BENZALDEHYDES

The reactivity of the amino group in S-thiocarbamoyl-, S-aroyl-, and S -(N-phenylbenzi-midoyl)thiohydroxylamines (1), (2), (3) were examined. Their benzoylation by benzoic anhydride and condensation with benzald ehydese were performed in order to compare the reactivity with other a mino compounds such as amines and carboxamides. Though they are less s table thermally and sensitive to acids, the corresponding N-benzoyl de rivatives (5a, b), (6) and a number of novel imine componds (7a approx imately d), (8a approximately h), (9a approximately c) were given even under mild conditions in fair yields, respectively. This fact suggest s that the amino group of these thiohydroxylamines are more reactive t han that of carboxamides. The imines (7), derived from (1), were found to have characteristic affinity for silver salts to form 1:1 adducts (10a approximately c).