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RESEARCH PRODUCT
Reaction Mechanism of an Intramolecular Oxime Transfer Reaction: A Computational Study
Jani O. MoilanenPetri M. PihkoAntti J. Neuvonensubject
chemistry.chemical_compoundReaction mechanismchemistryIntramolecular forceOrganic ChemistryDiastereomerFormaldehydeDensity functional theoryPhotochemistryOximeta116Polarizable continuum modelAcetone oximedescription
Density functional theory (PBE0/def2-TZVPP) calculations in conjunction with a polarizable continuum model were used to assess the mechanism of the intramolecular oxime transfer reaction that leads to the formation of isoxazolines. Different diastereomers of the intermediates as well as different oximes (formaldehyde and acetone oxime) were considered. The computed reaction profile predicts the water-addition and -expulsion steps as the highest barriers along the pathway, a conclusion that is in line with the experimental evidence obtained previously for these reactions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-02-13 | The Journal of Organic Chemistry |