Cubane: 50 Years Later

The fascination with elaborate molecular architectures that differ significantly from those ordinarily present in nature have motivated synthetic, physical organic, and theoretical chemists alike, to explore their distinct properties and to pursue novel applications. In addition, they noted that once the anion has been consumed, the amide can participate in an additional metalation, allowing for the access to doubly halogenated cubanes such as diiodocubecarboxamide. This was a significant discovery because the electron-withdrawing nature of cyano substituents on the cubane core with assistance from the amide moiety allows for a facile direct proton abstraction. It only requires a slight excess of base to give complete conversion. While the application of N,N-diisopropylcarboxamides were useful in the generation of lithiated cubane derivatives, in a variety of cases it was not advantageous to carry this functionality throughout the whole synthetic sequence.