Photosensitiser-controlled regioselectivity in the electron-transfer cycloreversion of 2,3-diphenyloxetanes.
The regioselectivity of the oxidative electron-transfer cycloreversion of trans,trans-2,3-diphenyl-4-methyloxetane is photosensitiser dependent. With chloranil the reaction proceeds through the trans-beta-methylstyrene radical cation; however, in the case of pyrylium salts, the trans-stilbene radical cation is formed.
Miranda
Miguel A
MA
Dpto. de Química-Instituto de Tecnología Química UPV-CSIC, Universidad Politècnica de Valencia, Camino de Vera s/n, 46022 Valencia, Spain. mmiranda@qim.upv.es
Izquierdo
M Angeles
MA
D001713:Biphenyl Compounds / Q000737:chemistry*; D002412:Cations; D002703:Chloranil / Q000737:chemistry*; D004579:Electron Transport; D004988:Ethers, Cyclic / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D007700:Kinetics; D010782:Photolysis; D017319:Photosensitizing Agents / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D013816:Thermodynamics
D001713:Biphenyl Compounds; D002412:Cations; D002703:Chloranil; D004988:Ethers, Cyclic; D005609:Free Radicals; D017319:Photosensitizing Agents; D011714:Pyrans; C010574:biphenyl; C005287:oxetane