Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)1

doi:10.1021/ja983441f

Paper

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)1

Published Apr 20, 1999 · DOI · P. Eaton, K. Pramod, T. Emrick

Journal of the American Chemical Society

48

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1

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Abstract

On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of “living polymerization” of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up of cubanes linked together at the 1 and 4 positions, each cubane adding ∼4.15 A to the length. The properties of these rods, some more than 15 A 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.

Study Snapshot

Cubane-1,4-diyl is a versatile precursor for synthesis of aryl-substituted cubanes, p-[n]cubyls, and bicubyl derivatives, with potential applications in organic synthesis and polymerization.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)1

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