86396-74-9Relevant academic research and scientific papers
PHOTOOXYGENATION OF 1,2-DIARYLCYCLOPROPANES: FORMATION OF 3,5-DIARYL-1,2-DIOXOLANES VIA PHOTOINDUCED ELECTRON TRANSFER
Mizuno, Kazuhiko,Kamiyama, Nobuhiro,Otsuji, Yoshio
, p. 477 - 480 (1983)
The photooxygenation of electron-rich 1,2-diarylcyclopropanes such as 1,2-bis(4-methoxyphenyl)cyclopropane and 1-(4-methoxyphenyl)-2-phenyl-cyclopropane in the presence of 9,10-dicyanoanthracene (DCA) as a sensitizer in acetonitrile affords trans- and cis-3,5-diaryl-1,2-dioxolanes in high yields.This photooxygenation is initiated by the electron transfer from 1,2-diarylcyclopropanes to the excited singlet DCA, involving the cation radical of cyclopropanes as a key intermediate.
PHOTO-OXYGENATION OF 1,2-DIARYLCYCLOPROPANES VIA ELECTRON TRANSFER
Mizuno, Kazuhiko,Kamiyama, Nobuhiro,Ichinose, Nobuyuki,Otsuji, Yoshio
, p. 2207 - 2214 (2007/10/02)
The photo-oxygenation of 1,2-diarylcyclopropanes bearing electron-donating substituents in the presence of 9,10-dicyanoanthracene (DCA) in acetonitrile affords trans- and cis-3,5-diaryl-1,2-dioxolanes in excellent yields.The DCA-sensitized photo-oxygenation of less electron-rich 1,2-diarylcyclopropanes gives various oxidation products in low yields.These photoreactions are greatly accelerated by the addition of certain aromatic hydrocarbons and metal salts, and are completely quenched by the addition of triethylamine and 1,4-diazabicyclooctane.No photo-oxygenation takes place in non-polar solvents.The electron transfer mechanism is proposed for the photo-oxygenations, in which the cation radicals of 1,2-diarylcyclopropanes are involved as chain carriers.
