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首页> 美国政府科技报告 >Stereoselective Formation of Cis Ozonides by Electron-Transfer Photooxygenation of Naphthyl-Substituted Epoxides. Stereochemical Assignments of Ozonides by X-Ray Crystallography and Chromatographic Resolution
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Stereoselective Formation of Cis Ozonides by Electron-Transfer Photooxygenation of Naphthyl-Substituted Epoxides. Stereochemical Assignments of Ozonides by X-Ray Crystallography and Chromatographic Resolution

机译：萘基取代环氧化物的电子转移光氧化立体选择性形成顺式臭氧化物。通过X射线晶体学和色谱分离的臭氧化物的立体化学分配

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9,10-Dicyanoanthracene sensitizes the electron-transfer photooxygenation of dinaphthyl-substituted epoxides in oxygen-saturated acetonitrile to form ozonides in high yield. Both cis and trans isomers of 2,3-bis (1'-naphthyl)oxirane, 2,3-bis(2'napththyl) oxirane, and 2-(1'-naphthyl)-3-(2'-naphthyl) oxirane are converted exclusively to the cis ozonides. The stereochemistry of the ozonides has been unequivocally assigned by an X-ray structure of cis-3,5-bis(2'-napththyl)-1,2,4-trioxolane. The corresponding trans ozonide was prepared by ozonation of cis-1,2-bis(2'-naphthyl)ethene and stereochemically identified by chromatographic resolution using high-performance liquid chromatography with optically active (+) -poly(triphenylmethyl methacrylate) as the stationary phase. These stereochemical results provide support for a proposed mechanism involving addition of singlet oxygen as a dipolarophile to intermediate carbonyl ylides. (Author)

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