Substituent effects on the symmetry-disallowed thermal ring opening of tetramethylbicyclo[2.2.0]hex-2-enes
β Scribed by F. van Ranwijk; H. van Bekkum
- Book ID
- 104226179
- Publisher
- Elsevier Science
- Year
- 1976
- Tongue
- French
- Weight
- 77 KB
- Volume
- 17
- Category
- Article
- ISSN
- 0040-4039
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The effect of substituents on the reactivity and stereoselectivity of the SmI 2 /Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne d
Silylated 2-and 3-chloroalkyl dithioketals were prepared from corresponding 2-lithio dithioketals with 1,2-and 1,3-dihaloalkanes. The functionalized 1,3-dithianes underwent an easy ring expansion reaction into 1,5-dithiacyclooct-2-enes in the presence of basic alumina in refluxing petroleum ether.