Abstract
Re(VII) oxides catalyze the acetalization, monoperoxyacetalization, monothioacetalization and allylation of hemiacetals. The reactions, which take place under mild conditions and at low catalyst loadings, can be conducted using hemiacetals, the corresponding O-silyl ethers, and, in some cases, the acetal dimers. Aldehydes react under similar conditions to furnish good yields of dithioacetals. Reactions of hemiacetals with nitrogen nucleophiles are unsuccessful. 1,2-Dioxolan-3-ols (peroxyhemiacetals) undergo Re(VII)-promoted etherification but not allylation. Hydroperoxyacetals (1-alkoxyhydroperoxides) undergo selective exchange of the alkoxide group in the presence of either Re2O7 or a Brønsted acid.
Original language | English (US) |
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Pages (from-to) | 1526-1532 |
Number of pages | 7 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 9 |
DOIs | |
State | Published - Jul 30 2013 |
Externally published | Yes |
Keywords
- Allylation
- Hemiacetal
- O,O-acetal
- O,S-thioacetal
- Peroxyacetal
- Re O
- S,S-acetal
ASJC Scopus subject areas
- Organic Chemistry