Insertion of Carboryne into Aromatic Rings: Formation of Cyclooctatetraenocarboranes

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• 作者：Sunewang R. Wang ; Zaozao Qiu ; Zuowei Xie
• 刊名：Journal of the American Chemical Society
• 出版年：2010
• 出版时间：July 28, 2010
• 年：2010
• 卷：132
• 期：29
• 页码：9988-9989
• 全文大小：176K
• 年卷期：v.132,no.29(July 28, 2010)
• ISSN：1520-5126

文摘

1-Iodo-2-lithiocarborane is an efficient precursor to carboryne. It can react with arenes to give different types of dearomatization products, [4+2] cycloaddition and/or cycloinsertion products, dependent upon the substituents on the aromatic rings. The formal cycloinsertion products, cyclooctatetraenocarboranes, is generated from the [2+2] cycloaddition intermediates followed by thermal [3,3] sigmatropic rearrangement. This novel dearomatization of arenes with carboryne also serves as an important method for the synthesis of cyclooctatetraenocarboranes.