Ring opening of cyclic ethers by sulfuric acid - acetic anhydride
β Scribed by Yasuhiro Tanoue; Moritsugu Hamada; Norihisa Kai; Takeshi Nagai; Kazunori Sakata; Mamoru Hashimoto; Shin-Ichi Morishita
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 2000
- Tongue
- English
- Weight
- 202 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0022-152X
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β¦ Synopsis
Abstract
Cyclic ethers such as tetrahydrofuran or tetrahydropyran were easily cleaved at room temperature by sulfuric acid β acetic anhydride providing the corresponding diacetoxyalkanes in good yield. The ring opening was applicable to saturated cyclic ethers, regardless of the presence of substituent groups.
π SIMILAR VOLUMES
Three unsubstituted cyclic ketene acetals (CKAs), 2-methylene-1,3-dioxolane, 1a, 2-methylene-1,3-dioxane, 2a, and 2-methylene-1,3-dioxepane, 3a, undergo exclusive 1,2addition polymerization at low temperatures, and only poly(CKAs) are obtained. At higher temperatures, ring-opening polymerization (RO
Ring-opening reactions of 1,3-dioxepan-2-one (1) and 1,3-dioxan-2-one (2) with several alcohols were examined. The reactions proceeded without trifluoroacetic acid (TFA) in low conversions, while they proceeded smoothly with TFA to afford the ring-opened adducts and oligomers. Ring-opening polymeriz