Kinetic and thermodynamic control in the intramolecular hydroxyl capture of seleniranium ions
β 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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β¦ 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.
π SIMILAR VOLUMES
## 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 5β or 6β__exo__βtet cyclization of hydroxy sulfides gave the kinetic products while the 6β__endo