Rearrangement of 1-amino-2-nitrocyclopentanecarboxylic acid during acetylation

Abstract

1-Amino-2-nitrocyclopentanecarboxylic acid and its N-acetyl derivative rearrange to 6-acetamido-1-acetyl-6-carboxypiperid-2-one during acetylation. The reaction is related to previously observed rearrangements of α-nitro-ketones, and in the present series the presence of both a carboxy- and an acetamido-group seems necessary. Cyclohexane analogues do not undergo the rearrangement. A possible reaction mechanism to account for these facts is discussed.