Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)
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- 作者：Philip E. Eaton ; Kakumanu Pramod ; Todd Emrick ; and Richard Gilardi
- 刊名：Journal of the American Chemical Society
- 出版年：1999
- 出版时间：May 5, 1999
- 年：1999
- 卷：121
- 期：17
- 页码：4111 - 4123
- 全文大小：331K
- 年卷期：v.121,no.17(May 5, 1999)
- ISSN：1520-5126
文摘
On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactivespecies, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for thefirst time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kindof "living polymerization" of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rodsmade up of cubanes linked together at the 1 and 4 positions, each cubane adding ~4.15 Å to the length. Theproperties of these rods, some more than 15 Å long, are discussed, as are methods for modifying their solubility.X-ray crystallographic analyses of some of these compounds are presented, with emphasis on packing parameters.