Abstract
The acid isomerization of N-acyl-2,2-dimethylaziridines
1
in concentrated sulfuric acid at room temperature leads to oxazolines
2
but the neutral hydrolysis of
1
in pure water at room temperature leads to amidoalcohols
3
. However, the use of aqueous solutions of H
2
SO
4
at different concentrations at room temperature leads to a mixture of oxazolines
2
, amidoalcohols
3
and allylamides
4
with yields depending on the acidity of the medium and the nature of the acyl group. A mechanism has been suggested to explain the formation of these three products. DFT calculations employing the Gaussian 09 program with DFT/B3LYP methods and 6-311++G(2d,2p) basis set were carried out which gave the most stable geometry as well as their atomic charge distributions of compounds
1-4
.
Graphical Abstract
The acidic aqueous solutions of the N-acyl-2,2-dimethylaziridines
1
lead to a mixture of oxazolines
2
, amidoalcohols
3
and methallylamides
4
. The mechanism proposed to explain the formation of products
2
-
4
have been confirmed by the quantum chemical calculations using the DFT/B3LYP method and 6-311++G(2d,2p) basis set.