Reactivity of Thiohydroxylamines toward Benzoic anhydride and Benzaldehydes.

Abstract

The reactivity of the amino group in S-thiocarbamoyl-, S-aroyl-, and S-(N-phenylbenzimidoyl)thiohydroxylamines ( 1 ), ( 2 ), ( 3 ) were examined. Their benzoylation by benzoic anhydride and condensation with benzaldehydes were performed in order to compare the reactivity with other amino compounds such as amines and carboxamides. Though they are less stable thermally and sensitive to acids, the corresponding N-benzokl derivatives (5 a, b), ( 6 ) and a number of novel imine componds (7 a--'d), (8 ah), (9 ac) were given even under mild conditions in fair yields, respectively. This fact suggests that the amino group of these thiohydroxylamines are more reactive than that of carboxamides. The imines ( 7 ), derived from ( 1 ), were found to have characteristic affinity for silver salts to form 1: 1 adducts (10 a -'c).