114424-49-6Relevant articles and documents
Salt Effect on the 9,10-Dicyanoanthracene-Sensitized Photooxygenation of 1,2-Diarylcyclopropanes and the Photodecomposition of 3,5-Diaryl-1,2-dioxolanes
Tamai, Toshiyuki,Mizuno, Kazuhiko,Hashida, Isao,Otsuji, Yoshio
, p. 5338 - 5342 (2007/10/02)
The 9,10-dicyanoanthracene (DCA)-sensitized photooxygenation of less electron-rich 1,2-diarylcyclopropanes 1 such as 1,2-diphenylcyclopropanes and 1,2-bis(4-chlorophenyl)cyclopropanes in the presence of Mg(ClO4)2 gave cis- and trans-3,5-diaryl-1,2-dioxolanes as major products.However, in the absence of Mg(ClO4)2, the photooxygenation did not afford 1,2-dioxolanes, but their decomposition products, 1,3-diaryl-1-hydroxypropan-3-ones 5, aryl aldehydes 6, and aryl methyl ketones 7.The DCA-sensitized photodecomposition of 1,2-dioxolanes also gave 5-7.This photoreaction was suppressed by addition of Mg(ClO4)2.The DCA-sensitized photooxygenation of 1 proceeds via radical cations that are generated by photoinduced electron-transfer from 1 to the excited singlet 1DCA*.The DCA-sensitized photodecomposition of 1,2-dioxolanes occurs via exciplexes that are formed between 1,2-dioxolanes and 1DCA* or energy-transfer from the excited triplet 3DCA* to 1,2-dioxolanes.
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 (2007/10/02)
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.
