Recently we observed that iodinated vinylcubane had a tendency to undergo cage opening/rearrangement to yield a styrene compound. It was in this finding that a cubyl styrene derivative was proposed in order to deter the cage opening of the cubane and thus perform polymerization from a vinylcubane-based monomer. Ultimately this cubyl styrene derivative underwent a more rapid cage opening/rearrangement than its none phenyl counterpart. The path to its opening was observed to initially form a tricyclooctadiene, followed by cyclooctatetraene, and finally the rearrangement to a �-iodo-styrene compound. In addition, an iodinated cubyl aldehyde was also examined and remarkably, benzyl benzoate was ultimately formed, suggesting an alternate fragmentation pathway.

Cage opening/rearrangement of iodinate cubane derivatives

243rd National Meeting (2012)

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