Phenol-exo spirocyclisations of phenolic iodides 7–9 have been shown to proceed smoothly in the 5- and 6-exo-tet senses; in contrast the phenolic epoxides 13–15 fail to cyclise in these formally allowed modes and only the 7-endo type, e.g.14a→16 is viable: cyclisation via phenylthiiranium ions follows a similar pattern.
D. Hobbs-Mallyon and D. A. Whiting, J. Chem. Soc., Perkin Trans. 1, 1991, 2277 DOI: 10.1039/P19910002277
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