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Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

ABSTRACT: [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.

SUBMITTER: Jasti R

PROVIDER: S-EPMC2487678 | biostudies-other | 2006 May

REPOSITORIES: biostudies-other

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Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.

Jasti Ramesh R Rychnovsky Scott D SD

Organic letters 20060501 10

[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. ...[more]

PMID: 16671810

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