What is the role of $\ce{AlCl3}$ in the following synthesis of adamantane? I'm guessing it functions as a Lewis acid, but I am unsure how the mechanism of the second step works, as there is no region of high electron density in the bicyclic species.

If a mechanism for the second step exists, I would greatly appreciate if someone could propose one.

adamantane synthesis

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    $\begingroup$ Tada, found it: chemistry.stackexchange.com/questions/57826/… Not the same question, but related. The reference in my first comment (Chem. Soc. Rev. 1974, 3, 479) hopefully contains more than enough info for an answer, if anybody is keen on writing an answer. $\endgroup$ Dec 8, 2017 at 12:48
  • $\begingroup$ The carbocation rearrangement mechanism is here: Schleyer, et al., J. Am Chem. Soc., 1973, 95, 5769. Too much to draw and I don't want to lift it from the paper. $\endgroup$
    – user55119
    Dec 8, 2017 at 16:26


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