Acylation of 2-amino-5,5-dimethyl-Δ1-pyrroline 1-oxide
Abstract
Acetylation and benzoylation of 2-amino-5,5-dimethyl-Δ1-pyrroline 1-oxide (I) gave 3-substituted products. Reaction mechanisms are discussed. Schotten–Baumann benzoylation of the same compound gave 2-benzamido-2-benzoyloxy-1-hydroxy-5,5-dimethylpyrrolidine (Xa), the derived 1,2-dibenzoate (Xb), and a 3-substituted by-product. Contrary to an earlier report, aryl isocyanates react with the pyrroline oxide (I) to give 2-arylcarbamoylimino-1-hydroxy-derivatives.