De Kimpe aziridine synthesis
| De Kimpe aziridine synthesis | |
|---|---|
| Named after | Norbert De Kimpe |
| Reaction type | Ring forming reaction |
| Identifiers | |
| Organic Chemistry Portal | de-kimpe-aziridine-synthesis |
The De Kimpe azirdine synthesis is a
The De Kimpe aziridine synthesis is suitable for both aldimines and ketimines, particularly those with two alkyl substituents on the α-carbon (
Thorpe-Ingold effect).[4]
Mechanism
The nucleophile attacks the imino carbon atom, forming a tetrahedral intermediate. The intermediate then undergoes an intramolecular nucleophilic substitution, with the negatively charged nitrogen atom attacking the α-carbon and having the chloride anion as the leaving group.
References
- .
- PMID 17397222.
- PMID 16805569.
- ^ de Kimpe, Norbert; Verhé, Roland; de Buyck, Laurent; Schamp, Niceas (1 January 1977). "Reaction of secondary N‐1‐(2‐chloroalkylidene)amines with lithium tetrahydridoaluminate: Synthesis and rearrangement of 1,2,2‐trisubstituted aziridines". Recueil des Travaux Chimiques des Pays-Bas. 96 (9): 242–246.
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