Azetidine
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| Template:Longitem | 102384 |
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| Template:Longitem | 986 |
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| Molar mass | 57.09 g/mol |
| Appearance | colorless liquid |
| Density | 0.847 g/cm3 at 25 °C |
| Boiling point | Template:Chembox CalcTemperatures |
| Acidity (pKa) | 11.29 (conjugate acid; H2O)[2] |
| Template:Longitem | Oxetane, Phosphetane, Thietane |
| Template:Longitem | Aziridine, Diazetidine, Pyrrolidine, Piperidine, Azepane, Azocane, Azonane |
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Azetidine is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly basic compared to most secondary amines.
Synthesis and occurrence
Azetidines can be prepared by reduction of azetidinones (β-lactams) with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH2" and "AlCl2H".[3] Azetidine can also be produced by a multistep route from 3-amino-1-propanol.[4]
Regio- and diastereoselective synthesis of 2-arylazetidines could be performed from appropriately substituted oxiranes via ring transformation. It is controlled by Baldwin's Rules with remarkable functional group tolerance.Script error: No such module "Unsubst".
The Paternò−Büchi reaction has an aza analogue.
Azetidine and its derivatives are relatively rare structural motifs in natural products. They are a component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid - a toxic mimic of proline.[5]
See also
- Azete, the unsaturated analog
References
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