2,4,6-Triisopropylbenzenesulfonyl hydrazide

Tarraga, A. Oton, F. Espinosa, A. Desamparados Velasco, M. Molina, P. Evans, D. J., Chem. Common. 2004, 458. 

Solubility sol virtually all ethereal, halogenated, protic, and apro-tic solvents insol water and hydrocarbon solvents. 

Richard Chamberlin James E. Sheppeck II University of Caiifornia, Irvine, CA, USA 

Alkene Reduction. 2,4,6-Triisopropylbenzenesulfonyl hydrazide (TPSH) undergoes solvent-dependent thermal degradation into diazene (diimide) between 35 and 65 °C, resulting in the in situ reduction of alkenes and other double bonds in good to excellent yields. TPSH remains one of the best sources of diazene, and addition of amine bases increases the rate of both diazene formation and hydrogenation. It is the most reactive of the common arenesulfonylhydrazides, being 380 and 24 times more reactive than /j-toluenesulfonylhydrazide and mesitylenesulfonylhy-drazide, respectively, under base-catalyzed conditions.  

Formation of Hydrazones. Much of the rich chemistry exhibited by TPSH comes from its condensation products with ketones and aldehydes. Such trisyl hydrazones are typically prepared in excellent yield by mixing equimolar amounts of reagents in methanol or ethanol at room temperature with a catalytic amount of acid such as HCl and storing the reaction in the cold. The product precipitates and is filtered off. Very hindered ketones such as camphor and diisopropyl ketone require stoichiometric amounts of acid and extraordinarily hindered ketones may not condense at aU.i  

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