Relative Stabilities of Some Synthetically Useful 2,3-cis-Disubstituted Aziridines and Their 2,3-Trans Isomers
The Journal of Organic Chemistry2002Vol. 67(16), pp. 5796–5801
Citations Over TimeTop 16% of 2002 papers
Abstract
The relative stabilities of synthetically useful 2,3-cis/trans pairs of 2,3-disubstituted aziridines were investigated theoretically by performing molecular orbital calculations at the MP2/6-31G**/RHF/6-31G** level of theory. The results showed clearly that a functional group on the nitrogen atom of the aziridine ring plays a very important role in conjunction with the relative stabilities of these pairs of isomers. There is a tendency that the 2,3-cis isomer bearing tetrahedral structure on the aziridine nitrogen is preferable. Bulky substituents such as a phenyl group on aziridine atoms can also affect the relative stability sterically.
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