Chemistry of the Sulfur-Nitrogen Bond. 12.1 Metal-Assisted Synthesis of Sulfenamide Derivatives from Aliphatic and Aromatic Disulfides

Abstract

The metal-assisted synthesis of sulfenamide derivatives 1 and 2 from aliphatic and aromatic disulfides and amines was explored. This method is more convenient and results in higher yields and a less reactive product than sulfenamides prepared from sulfenyl chlorides. Sulfenamides containing reactive functional groups, not accessible from sulfenyl chlorides, can be prepared using this procedure. With ammonia and aromatic disulfides this method yields bis(arenesulfen)imides 4 when the groups attached to sulfur are more electron donating than a 3, 4-dichloro-phenyl group. Alkanesulfenamides of ammonia (RSNH2) cannot be isolated, but are trapped with aromatic aldehydes and ketones to yield N-alkylidenealkanesulfenamides 2. © 1977, American Chemical Society. All rights reserved.