Balancing the transesterification reactivity of isosorbide with diphenyl carbonate: preferential activation of <i>exo</i>-OH
Ming Zhang, Yifei Tu, Zibo Zhou, Guozhang Wu
Abstract
<italic>Exo</italic>-OH on ISB has long been asserted as a highly reactive moiety compared with <italic>endo</italic>-OH. Herein, we report that the nucleophilic attack surmounts steric hindrance in rendering <italic>endo</italic>-OH more reactive than <italic>exo</italic>-OH in case of transesterification with DPC.
Topics & Concepts
Steric effectsChemistryReactivity (psychology)TransesterificationNucleophileMoietyMedicinal chemistryStereochemistryOrganic chemistryMethanolCatalysisPathologyAlternative medicineMedicineCarbon dioxide utilization in catalysisSynthesis and Biological EvaluationChemical Synthesis and Reactions