Mechanism of dicyanoanthracene-photosensitized oxygenation of 1, 1, 2, 2-tetraarylcyclopropanes and 1, 1, 3, 3-tetraarylpropenes

K Gollnick, XL Xiao, U Paulmann

Index: Gollnick, Klaus; Xiao, Xu-Ling; Paulmann, Uwe Journal of Organic Chemistry, 1990 , vol. 55, # 24 p. 5945 - 5953

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Citation Number: 22

Abstract

6a-e were irradiated in CCll and acetonitrile in the presence of oxygen and various sensitizers. The cyclopropanes as well as the propenes are inert toward singlet oxygen in both solvents. In electron-transfer-induced oxygenation reactions, photosensitized by 9, lO- dicyanoanthracene in acetonitrile, cyclopropanes 2d-f, carrying efficient electron-donating 4- methoxyphenyl and 4-phenoxyphenyl groups, yield 1, 2-dioxolanes 3d-f exclusively. ...