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This protocol demonstrates ring-opening rearrangement reactions to synthesize N-(2-chloropropyl)amides and 5-methyl-2-oxazolines, highlighting a novel mechanism involving aziridine intermediates.
A ring-opening rearrangement reaction of N-cyclopropylamides is shown to occur in the presence of AlCl3. The mechanism proposed herein involves the "Heine-type" aziridine intermediate and C-Cl or C-O bond formation. This protocol provides quick access to N-(2-chloropropyl)amides and 5-methyl-2-oxazolines using simple and readily available starting materials.
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Wan et al. (2025) studied this question.
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