The adduct (3) formed from adamantan-2-one and allyltrimethylsilyl anion (2) is converted by N-bromosuccinimide into the spiro-oxetan (4), which undergoes a number of elimination reactions to give (6), (7), and (8).
E. Ehlinger and P. Magnus, J. Chem. Soc., Chem. Commun., 1979, 421 DOI: 10.1039/C39790000421
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