Metallation of the acetal (H-2) proton in 1,3-dioxolanes, 1,3-dioxanes and open chain acetals is possible only if the proton can occupy an "equatorial-like" conformation.
Metallation of rigid 2-aryl-1,3-dioxanes
โ Scribed by Arthur L. Campbell; Ish Kumar Khanna
- Publisher
- Elsevier Science
- Year
- 1986
- Tongue
- French
- Weight
- 203 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Regioselective metallation and alkylation/acylation of 2-aryl-1,3-dioxanes was achieved in high yield.
๐ SIMILAR VOLUMES
The synthesis and the stereocbemistry of a new class of compounds showing atropisomerism, the 1,3-dioxane derivatives bearing disymmetric axial aryl groups in position 2 of the 1,3-dioxane ring are reported.
tie chair + chair equilibrium of 5-aryl-5-methyl-1,3-dioxanes, unlike that of 1-aryl-I-methylcyclohexanes, is remarkably sensitive to the nature of substituents on the aromatic ring. An interaction involving the the arcmatic group and the dioxane oxygen atoms or C-O bonds is proposed.