Controllable Synthesis of Two Isomers 4<i>H</i>-Chromene and 2,8-Dioxabicyclo[3.3.1]nonane Derivatives under Catalyst-Free Conditions
Shuang Wang, Jun-Jie Lin, Xin Cui, Jingpeng Li, Chao Huang
Abstract
A one-pot method for the selective synthesis of two isomers 4H-chromene and 2,8-dioxabicyclo[3.3.1]nonane derivatives was developed without a catalyst and using EtOH/H2O (4:1, v/v) as the solvent. The reaction was conducted under mild conditions, with forming multiple chemical bonds in one pot and high atom economy, and only a stoichiometric amount of H2O is produced as the byproduct. Its selectivity was controlled by thermodynamics and kinetics, and the reasons for the transformation of the two structures are also discussed.
Topics & Concepts
NonaneChemistryCatalysisSelectivityStoichiometryAtom economySolventKineticsReaction conditionsOrganic chemistryComputational chemistryQuantum mechanicsPhysicsCarbohydrate Chemistry and SynthesisSynthetic Organic Chemistry MethodsSynthesis of Organic Compounds