6533b820fe1ef96bd1279b68

RESEARCH PRODUCT

Photochemical Functionalization of Allyl Benzoates by C-H Insertion

Silvestre BuscemiAntonio Palumbo-piccionelloIvana PibiriGiampaolo BaroneAndrea Pace

subject

chemistry.chemical_classificationAllylic rearrangementDouble bondChemistryOrganic ChemistryMechanistic organic photochemistrySubstrate (chemistry)Organic photochemistryPhotochemical synthesis THF reactivityBiochemistryMedicinal chemistryC-C bond formationDFTBenzoatesSolventDrug DiscoverySurface modificationReactivity (chemistry)C-H insertion

description

The photoreactivity of allyl benzoates, containing an electron-rich double bond, has been explored by irradiation at 305 nm in different solvents. Solvent addition products arising from an insertion of the alpha H–C bonds of THF, dioxane, and i-PrOH to the allylic double bond was realized. The observed reactivity depended on reaction conditions and substitution pattern of the substrate. A DFT study on this unusual reaction was performed allowing the formulation of two mechanistic pathways.

yearjournalcountryeditionlanguage
2013-07-01
10.1016/j.tet.2013.05.093http://hdl.handle.net/10447/88646