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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/24235

Title: The Synthesis and Applications of N-alkenyl Aziridines
Authors: Afagh, Nicholas A.
Advisor: Yudin, Andrei
Department: Chemistry
Keywords: Aziridine
N-Alkenyl Aziridine
Issue Date: 5-Apr-2010
Abstract: N-alkenyl aziridines are a unique class of molecules that do not behave as typical enamines as a result of the inability of the nitrogen atom lone-pair of electrons to delocalize. The attenuated nucleophilicity of these enamines presents opportunities for selective functionalization and reactivity not available to classical enamines. An operationally simple and mild copper-mediated coupling has been developed that facilitates the preparation of a broad range of N-alkenyl aziridines not available through existing methods. The preparation and reactivity of highly functionalized N-alkenyl aziridines are reported. Also reported is the application of the chemoselective amine/aldehyde/alkyne (A3) multicomponent coupling involving amphoteric aziridine aldehydes as the aldehyde component. This coupling allows access to propargyl amines with pendent aziridine functionality.
URI: http://hdl.handle.net/1807/24235
Appears in Collections:Master
Department of Chemistry - Master theses

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