22.47 Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored at room temperature. Aziridine is a three-membered heterocycle containing a nitrogen atom. The following is an example of a chiral aziridine. In this compound, the nitrogen atom is a chiral center. Suggest a reason why chiral aziridines do not undergo racemization at room temperature.
22.47 Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored at room temperature. Aziridine is a three-membered heterocycle containing a nitrogen atom. The following is an example of a chiral aziridine. In this compound, the nitrogen atom is a chiral center. Suggest a reason why chiral aziridines do not undergo racemization at room temperature.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section21.4: Phenols
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