An efficient carbonyl-alkene metathesis of bicyclic oxetanes: photoinduced electron transfer reduction of the Paternò-Büchi adducts from 2,3-dihydrofuran and aromatic aldehydes.
The bicyclic oxetanes and resulting from photocycloaddition of aromatic aldehydes to 2,3-dihydrofuran, were efficiently cleaved by means of electron-transfer reduction, photoinduced by the electronically excited reductants 1-methoxynaphthalene (MN) and 2,7-dimethoxynaphthalene (DMN) in acetonitrile. The fluorescence quenching rates of DMN/MN by and were determined by static methods, the triplet quenching rates were determined by means of laser flash photolysis (LFP). The product analysis established a "photo-photo metathesis" where both cycloaddition and cycloreversion processes are induced by photochemical processes.
Pérez-Ruiz
Raúl
R
Departamento de Quimica/Instituto de Tecnologia Quimica UPV-CSIC, Universidad Politecnica de Valencia, Camino de Vera s/n, Apdo. 22012, 46022, Valencia, Spain.
Miranda
Miguel A
MA
Alle
Ronald
R
Meerholz
Klaus
K
Griesbeck
Axel G
AG
D000447:Aldehydes / Q000737:chemistry* / Q000528:radiation effects; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D003500:Cyclization; D004579:Electron Transport / Q000528:radiation effects; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D005663:Furans / Q000737:chemistry* / Q000528:radiation effects; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D013237:Stereoisomerism; D013816:Thermodynamics; D014466:Ultraviolet Rays
D000447:Aldehydes; D000475:Alkenes; D004988:Ethers, Cyclic; D005663:Furans; C073812:2,3-dihydrofuran