Mechanistic insights into hydroxy(tosyloxy)iodobenzene-mediated ditosyloxylation of chalcones: a DFT study.

ABSTRACT: In this paper, the mechanism of the hydroxy(tosyloxy)iodobenzene (HTIB)-mediated conversion of chalcones (α,β-unsaturated carbonyl compounds) to ditosyloxy ketones is investigated. Here, at β-carbon of the chalcone, an aryl group with a para-substituent is present. Our study focuses on investigating the effect of different nature of para-substituents on the reaction mechanism. The substituents considered in the study include -OCH₃, -SCH₃, -Cl and -NO₂ groups. For these chalcones, different possible pathways at various steps during the reaction are investigated leading to formation of α,β-ditosyloxy ketones and β,β-ditosyloxy ketones. It is found that the mechanism for the formation of α,β-ditosyloxy ketone involves only electrophilic addition

SUBMITTER: Parkash J 

PROVIDER: S-EPMC12719883 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature