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The tricyclic anion 5, generated from the corresponding hydrocarbon 3 with n-BuLi, undergoes the circumambulatory rearrangement at −78 °C to afford the anion 6, which stereoselectively reacts with deuterium oxide at low temperature and undergoes further rearrangements to the stable cyclopentadienyl anion derivative 9 at elevated temperature.
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Oda et al. (1997) studied this question.
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