Premium
Fundamental properties of N ‐alkenylaziridines—implications for the design of new reactions and organocatalysts
Author(s) -
Siebert Matthew R.,
Tantillo Dean J.
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1776
Subject(s) - iminium , chemistry , reactivity (psychology) , enamine , organocatalysis , ion , computational chemistry , cyclic amines , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , medicine , alternative medicine , pathology
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. Copyright © 2010 John Wiley & Sons, Ltd.