In 1929, the conversion of oleic acid to stearic acid in the presence of hydrazine was observed. The short-lived intermediate diimide was not implicated in this reductive process until the 1960s. Since that time, several methods of generating transient amounts of diimide have been developed. In the presence of unpolarized alkenes, alkynes or allenes, diimide is converted into dinitrogen with reduction (net addition of dihydrogen) of the unsaturated functionality. Diimide formation is the rate-limiting step of the process, and a concerted mechanism involving cis-diimide has been proposed. This reduction represents a metal-free alternative to catalytic hydrogenation reductions, and does not lead to the cleavage of sensitive O–O and N–O bonds.