Circumtrindene: A Geodesic Dome of Molecular Dimensions. Rational Synthesis of 60 of C60

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• 作者：Ronald B. M. Ansems and Lawrence T. Scott
• 刊名：Journal of the American Chemical Society
• 出版年：2000
• 出版时间：March 29, 2000
• 年：2000
• 卷：122
• 期：12
• 页码：2719 - 2724
• 全文大小：163K
• 年卷期：v.122,no.12(March 29, 2000)
• ISSN：1520-5126

文摘

The title compound (1), which had previously been available in only 0.2% yield by flash vacuumpyrolysis (FVP) of decacyclene (2) at 1200-1300 mages/entities/deg.gif">C, has now been prepared in 25-27% yield by FVP of3,9,15-trichlorodecacyclene (5b) at 1100 mages/entities/deg.gif">C. The propeller-shape 5b was synthesized by aldol cyclotrimerizationof 8-chloro-1(2H)-acenaphthylenone (8b), which, in turn, was prepared by a simple four-step synthesis from2-chloronaphthalene. The synthetic strategy demonstrated here, which has improved the yield of circumtrindene(1) by more than 2 orders of magnitude, should be applicable to the rational synthesis of larger geodesicpolyarenes, both open (bowls, baskets, tubes, etc.) and closed (fullerenes).