Abstract
The inexpensive and commercially available FeCl3 catalyzes the selective homo-aldol condensation of aldehydes into the corresponding α-β unsaturated aldehydes, presumably through an unobserved aldol intermediate. Surprisingly the reaction course can be diverted to produce 1,3,5-trioxanes via aldehyde cyclotrimerization. Selectivity for trioxanes is achieved at lower temperatures and is enhanced by the presence of water, contrary to prior reports. A broad range of aliphatic and aromatic aldehydes are capable of undergoing these transformations; short reaction times, high yields, scalability, and easy purification processes are also described.
Original language | English |
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Pages (from-to) | 2406-2411 |
Number of pages | 6 |
Journal | Tetrahedron Letters |
Volume | 56 |
Issue number | 19 |
DOIs | |
State | Published - May 6 2015 |
Keywords
- Aldehydes
- Aldol reactions
- Catalysis
- Cyclotrimerization
- Lewis acid