Oxyfunctionalization of Non-Natural Targets by Dioxiranes. 6. On the Selective Hydroxylation of Cubane

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• 作者：Cosimo Annese ; Lucia D’ ; Accolti ; Caterina Fusco ; Remo Gandolfi ; Philip E. Eaton ; Ruggero Curci
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：August 20, 2009
• 年：2009
• 卷：11
• 期：16
• 页码：3574-3577
• 全文大小：157K
• 年卷期：v.11,no.16(August 20, 2009)
• ISSN：1523-7052

文摘

By using methyl(trifluoromethyl)dioxirane (TFDO), the direct mono- and bishydroxylation of cubane could be achieved in high yield under remarkably mild conditions. Comparison of the rates of dioxirane O-insertion with those of standard reference compounds, such as adamantane and cyclopropane, as well as ab initio computations provide useful hints concerning the mechanism of these transformations.