226896-62-4Relevant articles and documents
Building with cubane-1,4-diyl. Synthesis of aryl-substituted cubanes, p- [n]cubyls, and cubane-separated bis(arenes)
Eaton, Philip E.,Pramod, Kakumanu,Emrick, Todd,Gilardi, Richard
, p. 4111 - 4123 (2007/10/03)
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 to cubanes linked together at the 1 and 4 positions, each cubane adding ~4.15 ? to the length. The properties of these rods, some more than 15 ? 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.