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Kinetic and thermodynamic control in the intramolecular hydroxyl capture of seleniranium ions

✍ Scribed by Michelangelo Gruttadauria; Renato Noto


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
265 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


The formation of tetrahydrofurans and tetrahydropyrans by acid catalyzed cyclization of hydroxy selenides can be explained by kinetic and thermodynamic control. The tetrahydropyrans from the hybrid 7-endo/6-exo cyclization are the thermodynamic products of the acid catalyzed cyclization of hydroxy selenides 1, whereas the tetrahydrofurans from the 5-exo cyclization are the kinetic products.


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Kinetic and thermodynamic control in the
✍ Michelangelo Gruttadauria; Renato Noto πŸ“‚ Article πŸ“… 2001 πŸ› Journal of Heterocyclic Chemistry 🌐 English βš– 38 KB

## Abstract The stereoselective rearrangement of tetrahydrofuran or tetrahydropyran rings having a phenylsulfanyl group in an __exo__ position, __via__ the intermediate thiiranium ions, is reported. The 5‐ or 6‐__exo__‐tet cyclization of hydroxy sulfides gave the kinetic products while the 6‐__endo