On exposure to n-butyl-lithium, 1,2-di-iodoadamantane yields the highly strained bridgehead olefin adamantene, which can be intercepted in a Diels–Alder reaction with butadiene at –78 °C; in the absence of butadiene it dimerises spontaneously in a [2 + 2] fashion.
W. Burns, D. Grant, M. A. McKervey and G. Step, J. Chem. Soc., Perkin Trans. 1, 1976, 234 DOI: 10.1039/P19760000234
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