Ortho Substituent Effect of the Side-Chain Phenyl Group on the Dehydrogenation of Flavanones with 2,3-Dichloro-5,6-dicyano-p-benzoquinone

Article abstract of DOI:10.1246/bcsj.60.4468

Rates of the dehydrogenation of 2'-substituted flavanones with 2,3-dichloro-5,6-dicyano-p-benzoquinone were measured by means of HPLC analyses.All substituents at the ortho position of the side-chain phenyl group of flavanones showed a retarding effect on the reaction.A correlation analysis for the ortho effect using the linear combination model has led to a conclusion that the inductive effect is much more important than the steric and the resonance effect, and that the steric effect is slightly greater than the resonance effect.