Fundamental Properties of N-Alkenylaziridines - Implications for the Design of New Reactions and Organocatalysts

Abstract

The success of many organocatalysts depends on the proper modulation of electronic properties of amines and their derived enamines and iminium ions. We and others have been fascinated with the differences in reactivity observed for aziridines versus other amines in many reactions. Herein we report a theoretical assessment (using B3LYP/6‐31 + G(d,p)) of the π‐donating ability of aziridines relative to other amines and discuss the implications for enamine and iminium ion reactivity.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1002/poc.1776

Keywords

N‐alkenylaziridine, organocatalysis, B3LYP, DFT

Publication Date

2010

Journal Title

Journal of Physical Organic Chemistry

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