Cubane is a molecule that has caught the attention of chemists due to its paradoxical nature, namely a high stability even though it contains multiple 90° bond angles. Typically, a ring system with a bond angle below 109.5° becomes unstable the lower the angle is, but cubane remains highly stable in spite of these structural features. These bond angles do contribute to cubane being extremely energetic where a large amount of energy is released when the bonds are broken. The molecule was first theorized to be possible by Wiliam Weltner Jr. in 1953, it was originally named tricyclooctane. Eaton and Cole synthesized this 11 years later, however the overall yield was abysmally low (around 12%) due to the long synthesis pathway used. Over time this was improved, and the current yields of cubane are around 47%. Yields remain low due to the photochemical step required to create the cube, where a α-halo ketone undergoes nucleophilic substitution (Favorskii rearrangement) which is typically used to convert cyclohexane rings into cyclopentane rings. For this rearrangement to occur UV-B light is needed, however, such lamps are costly. Cheaper commercial UV sources can be used, but doing so reduces the speed of the reaction and makes it prone to side reactions contaminating the product. For this reason, new methods are being developed to enable this reaction to occur in UV-A light that is safer and less expensive. In this work, the synthesis of cubane methyl ester was performed, the photochemical step was modified to see any improvements could be made, and products of this synthesis were all characterized by NMR.
Cubane: A Stable Molecule with Unstable Bonds – Advances in Synthesis and Characterization
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