Thermo-cage opening of 4-iodo-1-vinylcubane to a novel styrene derivative

Cubane (1) and its derivatives have been cited for exhibiting unusual properties, including explosive and antiviral activity. An additional characteristic of these compounds is their tendency to undergo cage opening under certain conditions. In our attempt to polymerize 4-iodo-1-vinylcubane (4), 4-vinyl-trans-β-iodostyrene (10) was formed quantitatively. By examining both the thermolytic and Lewis acid-assisted rates, a possible mechanism for the rearrangement of 4→10 has been proposed.