Tosylhydrazone

Organic compounds having this functional group can be accessed by reaction of an aldehyde or ketone with tosylhydrazine.

[2] Hydrolysis is the reverse reaction of formation with regeneration of the carbonyl compound.

Tosylhydrazones can be reduced to the corresponding alkanes with reagents such as sodium borohydride and borane.

[3][4] An example of a transition metal-catalyzed cyclopropanation is a synthesis of tranylcypromine,[5][6] in which the sodium salt of benzaldehyde tosylhydrazone is converted to a rhodium metal carbene through the diazo intermediate.

[7] In the first report on this reaction type the coupling partners were a tosylhydrazone, an aryl halide with catalyst system dibenzylideneacetone / XPhos.