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Hydrogenation with Diimide

Reduction with Diimide: Introduction.

Reaction principle

Diimide, a labile hydrogen donor, transfers hydrogen to the double bond leaving nitrogen behind. The reaction passes through a pericyclic transition state. In compounds with multiple double bonds, only the terminal double bond is reduced selectively. The reaction proceeds syn-stereospecific .




Diimide can be easily prepared in situ from potassium azodicaboxylate. For the reduction of small amounts of alkene, this reagent is easier to handle than hydrogen. Frequently, it is being used for the selective syn-deuterogenation of alkenes.

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