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RESEARCH PRODUCT
The role of the transfer group in the intramolecular [5+2] cycloadditions of substituted β-hydroxy-γ-pyrones: a DFT analysis
Luis R. DomingoMaría José AurellRamón J. Zaragozásubject
chemistry.chemical_classificationTransfer (group theory)chemistryYlideGroup (periodic table)StereochemistryIntramolecular forceOrganic ChemistryDensity functional theoryPhysical and Theoretical ChemistryCycloadditiondescription
The intramolecular [5+2] cycloaddition reactions of a series of 3-OR (R=SiMe3, H, CHO, Me) substituted β-hydroxy-γ-pyrones bearing tethered alkenes were studied using DFT methods at the B3LYP/6–31G* level. The role of the transfer R group was analyzed considering two alternative channels: (i) in channel a the process is initialized by the transfer of the R group with formation of an oxidopyrylium ylide intermediate, which is followed of an intramolecular [5+2] cycloaddition; (ii) in channel b, the process is initialized by the intramolecular [5+2] cycloaddition on the γ-pyrone followed by the transfer of the R group. Copyright © 2005 John Wiley & Sons, Ltd.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2005-07-01 | Journal of Physical Organic Chemistry |