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[reaction: see text] A solvolysis reaction is used to demonstrate that a tetrahydropyranyl cation is a common intermediate for Prins cyclizations, 2-oxonia-Cope rearrangements, and Grob fragmentations of tetrahydropyran rings.

Solvolysis of a Tetrahydropyranyl Mesylate: Mechanistic Implications for the Prins Cyclization, 2-Oxonia-Cope Rearrangement, and Grob Fragmentation