Diimide and Related Reductions

Diimide reduction of alkenes and alk3mes are also group transfer reactions. Delivery of two hydrogen atoms to an alkyne or alkene takes place in a concerted process involving suprafacial delivery of two hydrogens in a TS. These reactions are per-icyclic in nature. 

Diimide is unstable species and is generated in situ by oxidation of hydrazine and its derivatives. Common methods for generation of diimide are [32]  

Diimide reduction is a metal-ffee catalytic hydrogenation process and does not cleave the sensitive 0-0 and N-O bonds in the substrate. Diimide reduces symmetrical double bonds, e.g., C=C, N=N, 0=0, etc. 

Selectively reduces less substituted double bond 99% 

Among other group transfer reactions, the reduction of 1,2-dimethylcyclohexene with 9,10-dihydronaphthalene is used frequently [4]. 

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