Chemical Properties
White crystal
Uses
2,4,6-Triisopropylbenzenesulfonyl hydrazide (TPSH) is a best source of diazene. It can be used as a selective reducing agent for the reduction of alkenes and other double bonds via in situ formation of diazene (diimide) in the presence of base. TPSH reduction method is efficiently used in the synthesis of polymers and natural products as it tolerates sensitive groups such as esters, ketones, or organometal complexes. It also undergoes condensation reaction with ketones and aldehydes to produce corresponding hydrazones that can be converted into reactive intermediates such as diazoalkanes, carbenes, carbenium ions, and alkyllithiums.
It can be used as a reagent to synthesize:
- Nitrogen-containing polycyclic compounds by intramolecular cyclopropanation of N-alkyl indoles/pyrroles.
- Vinyl sulfones by sulfonylation reaction of vinyl bromides.
- Nitrile derivatives from carbonyl compounds via formation of corresponding hydrazones.
Uses
As a reagent for generation of diimide
Application
2,4,6-Triisopropylbenzenesulfonyl hydrazide is used as a diazene equivalent; condensed with ketones and aldehydes to form hydrazones that can be converted into reactive intermediates such as diazoalkanes, carbenes, carbenium ions, alkyllithiums, or umpolung synthons.
Preparation
2,4,6-Triisopropylbenzenesulfonyl hydrazide may be prepared in 96% yield by treating commercially available 2,4,6-triisopropylbenzenesulfonyl chloride with hydrazine hydrate in THF, being careful to keep the reaction and workup temperatures below or around 0 °C. The solid can be dried in vacuo over P2O5 for 24 h.
