| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Electron-Transfer Reactions of Aromatic α,β-Epoxy Ketones: Factors That Govern Selective Conversion to β-Diketones andβ-Hydroxy Ketones
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - Photoreaction oftrans-1-(4-cyanophenyl)-3-phenyl-2,3-epoxy-1-propanone(trans-4‘-cyanochalconeepoxide) with various electron donors was studied. Irradiation ofthis epoxy ketone with aminesproduced 1-(4-cyanophenyl)-3-phenyl-1,3-propanedione and1-(4-cyanophenyl)-3-hydroxy-3-phenyl-1-propanone in various ratios depending on the kinds of amine andsolvent used. A reactionmechanism involving an amine cation radical-assisted rearrangement ofthe epoxy ketone anionradical was proposed to be most consistent with the marked change inthe yield of β-diketone. Onthe other hand, the timing of proton transfer to the anionicintermediates is considered to be a keyfactor to yield the β-hydroxy ketone. Information obtained fromthe photochemical study was usefulto find the reaction conditions for the conversion of several aromaticepoxy ketones to hydroxyketones by the use of samarium diiodide. Addition of methanolsignificantly changed the productdistribution. Proper choice of water or methanol as a protonsource produced hydroxy ketones inmoderate to good yields.
|
| article type
| |
| is part of this journal
| |
