De Kimpe aziridine synthesis

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| Name = De Kimpe aziridine synthesis

| Type = Ring forming reaction

| NamedAfter = Norbert De Kimpe

| Section3 = {{Reactionbox Identifiers

| OrganicChemistryNamed = de-kimpe-aziridine-synthesis

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The De Kimpe aziridine synthesis is a name reaction of organic chemistry, for the generation of aziridines by the reaction of α-chloroimines with nucleophiles such as hydride,{{cite journal |last1=De Kimpe|first1=Norbert |last2=Moens|first2=Luc|date=6 February 1990|title=Synthesis of 1,2,3-trisubstituted and 1,2,2,3-tetrasubstituted aziridines from α-chloroketimines|url= |journal=Tetrahedron|volume=46|issue=8|pages=2965–2974|doi= 10.1016/S0040-4020(01)88388-5|access-date=}} cyanide, or Grignard reagents.{{cite journal |last3=De Kimpe|first3=Norbert|date=31 March 2007|title=Asymmetric Synthesis of Aziridines by Reduction of N-tert-Butanesulfinyl α-Chloro Imines|url= |journal=The Journal of Organic Chemistry|volume=72|issue=9|pages=3211–3217|doi=10.1021/jo0624795|pmid= 17397222|access-date=}}{{cite journal |last1=Denolf|first1=Bram|last2=Mangelinckx|first2=Sven|last3=Törnroos|first3=Karl W.|last4=Norbert|first4=De Kimpe|date=14 June 2006|title=Use of α-Chlorinated N-(tert-Butanesulfinyl)imines in the Synthesis of Chiral Aziridines|url= |journal=Organic Letters|volume=8|issue=14|pages=3129–3132|doi=10.1021/ol0611245|pmid=16805569|access-date=}}

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).{{cite journal |last1=de Kimpe|first1=Norbert|last2=Verhé|first2=Roland|last3=de Buyck|first3=Laurent|last4=Schamp|first4=Niceas|date=1 January 1977|title=Reaction of secondary N-1-(2-chloroalkylidene)amines with lithium tetrahydridoaluminate: Synthesis and rearrangement of 1,2,2-trisubstituted aziridines|url= |journal=Recueil des Travaux Chimiques des Pays-Bas|volume=96|issue=9|pages=242–246|doi= 10.1002/recl.19770960908|access-date=}}

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

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Category:Name reactions

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