One method for the synthesis of 9,9-spirobifluorenes

Chapter 19, Problem 19.92

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One method for the synthesis of 9,9-spirobifluorenes (rigid compounds with application to molecular electronics and light-emitting materials) involves protonation of ketone 1 with a catalytic amount of aqueous acid. Protonation of the CRO group generates an extremely powerful electrophile that facilitates a spontaneous cyclization (Org. Lett. 2004, 6, 23812383). Propose a plausible mechanism for this transformation. Br O Br OMe OMe H3O+ Br OMe Br MeO

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