Perfluoroaryltetrahedranes: Tetrahedranes with Extended σ−π Conjugation

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• 作者：Masaaki Nakamoto ; Yusuke Inagaki ; Motoaki Nishina ; Akira Sekiguchi*
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：March 11, 2009
• 年：2009
• 卷：131
• 期：9
• 页码：3172-3173
• 全文大小：128K
• 年卷期：v.131,no.9(March 11, 2009)
• ISSN：1520-5126

文摘

The first stable aryl-substituted tetrahedrane derivatives 4−6 were synthesized by the reaction of tris(trimethylsilyl)tetrahedranyllithium with hexafluorobenzene or [(pentafluorophenyl)ethynyl]benzene in THF. Tetrahedranes having the fluoroaryl groups as electron-withdrawing substituents were found to be thermally stable up to 170 °C. X-ray analyses of 4 and 6 and UV−vis absorption spectra of 4−6 suggest σ−π conjugation between the strained tetrahedrane core and the benzene ring, which causes a considerable bathochromic shift.