Strain Effects. II. Diimide Reductions of Olefins

Homogeneous Hydrogenation Art of Nitrile Butadiene Rubber: A Review

“…Generally, the order of the reactivity of these three types of C C is vinyl > cis > trans using an Rh catalyst 29 while the order changes to vinyl > cis ≈ trans in the hydrazine/oxidant-induced diimide hydrogenation reaction. [30][31][32][33] The vinyl-C C are more reactive towards chemical modification reactions than 1, 4 units due to their lower steric hindrance.…”

Étude DFT des réactions d’hydrogénation des cyclohéxènes disubstitués en position 2 et 3

“…[23][24][25][26][27] Ces études ont été réalisées sur l'hydrogénation des alcènes non cycliques tels que les molécules d'éthène et de propène. Dans le cas d'hydrogénation de 2b-2c par 1, lors de l'approche des réactifs, il y a des effets de gène sté-rique qui apparaissent.…”

Reductions of CC and CC by Noncatalytic Chemical Methods

“…Substituted allenes readily undergo reduction with diimide to produce alkenes, which undergo further slower reduction to alkanes.31,32 The diimide preferentially approaches the allene chromophore from the less hindered side of the less substituted double bond to produce the alkene having the cis stereochemistry as is illustrated by the reductions of allenes (34) and (37) in equations (14)32 and (15). 33 The reactivity of the allene chromophore towards reduction by diimide appears to be only slightly greater than that of the product alkenes; however, extensive overreduction occurs in the presence of the highly electronegative carboxylic acid functional group, as illustrated in equation (15).…”