Hydrogenolysis of Aryl p-Toluenesulphonates with Hydrazine in presence of Palladium

Abstract

Hydrogenolysis of aryl tosylates with hydrazine in presence of palladium catalyst involves a preliminary decomposition of hydrazine to give inter alia hydrogen, which then accomplishes the hydrogenolysis. The reaction can be carried out with molecular hydrogen in the presence of the same catalyst but not under reaction conditions involving the intervention of di-imide as the reactive species. Mono-nuclear aryl tosylates cannot be successfully hydrogenolysed with hydrazine over palladium. A novel method was established of generating di-imide from hydrazine and iodine in presence of base or excess hydrazine.