Cage opening and rearrangement of 1-iodocubane-4-carboxaldehyde

Cubane is a highly strained unsaturated molecule that was first synthesized in 1964 by Philip E. Eaton. Since cubane’s discovery, it has been researched in pharmaceuticals, explosives, and polymers. Due to its range of uses, we have explored the thermo-stability of a number of cubane derivatives. Some derivatives have revealed its propensity to undergo cage opening/rearrangement. In examining 1-iodocubane-4-carboxaldehyde, we observed that benzoic acid, benzaldehyde, benzyl alcohol, and benzyl benzoate were surprisingly formed in this thermo-decay.