During a recent study of epibatidine, a powerful analgesic

Chapter 23, Problem 23.97

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During a recent study of epibatidine, a powerful analgesic isolated from an Ecuadorian poison dart frog, the investigators employed an interesting fragmentation reaction to access ring-opened analogues (J. Org. Chem. 1999, 64, 49664968). Propose a plausible mechanism for the following transformation: N OH N Cl Cl CO2Et CO2Et HO CF3 O NaBH3CN N N

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