Substituent Effects on the Diimide Reduction of Dienes:Relative Reactivity of two Olefin Centers with a Differently Substituted Derivative

摘要

Diimide,HN=NH,an unstable hydrogen donor that can only be generated in situ,finds broad application in the reduction of C=C bonds.One of the advantages of diimide reduction is not undergoing hydrogenolysis as is often the case with catalytic hydrogenations.The mechanism of the reaction is known to involve hydrogen transfer of(Z)-diimide via a nonpolar cyclic transition state and the stereochemistry of addition is syn.