6533b860fe1ef96bd12c3179
RESEARCH PRODUCT
A molecular electron density theory study of the mechanism, chemo- and stereoselectivity of the epoxidation reaction of R -carvone with peracetic acid
Mar Ríos-gutiérrezOuafa AmiriLuis R. DomingoMohammed El IdrissiAbdellah Zeroualsubject
chemistry.chemical_classificationCarvoneElectron densityDouble bondGeneral Chemical Engineeringchemistry.chemical_element02 engineering and technologyGeneral Chemistry010402 general chemistry021001 nanoscience & nanotechnologyRing (chemistry)01 natural sciencesOxygen0104 chemical scienceschemistry.chemical_compoundchemistryComputational chemistryPeracetic acidStereoselectivityChemoselectivity0210 nano-technologydescription
The epoxidation reaction of R-carvone 8 with peracetic acid 9 has been studied within the molecular electron density theory at the B3LYP/6-311(d,p) computational level. The chemo- and stereoisomeric reaction paths involving the two C–C double bonds of R-carvone 8 have been studied. DFT calculations account for the high chemoselectivity involving the C–C double bond of the isopropenyl group and the low diastereoselectivity, in complete agreement with the experimental outcomes. The Baeyer–Villiger reaction involving the carbonyl group of R-carvone 8 has also been analysed. A bonding evolution theory analysis of the epoxidation reaction shows the complexity of the bonding changes taking place along this reaction. Formation of the oxirane ring takes place asynchronously at the end of the reaction by attack of anionic oxygen on the two carbons of the isopropenyl C–C double bond.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-09-10 | RSC Advances |