Direct Conversion of Arylamines to the Corresponding Halides, Biphenyls, and Sulfides with <i>t</i>-Butyl Thionitrate

Abstract

Abstract t-Butyl thionitrate have been found to be an excellent diazotizing reagent of arylamines in aprotic nonpolar media, affording eventually such products as aryl chlorides, aryl bromides, aryl iodides, biphenyls, and aryl methyl sulfides in the presence of CCl4, CHBr3, I2, benzene, and dimethyl disulfide, respectively, via extrusion of N2.