Formation of Nitronic Acids by Ring Opening of Nitrocyclopropanes by a Concerted, Acid-Catalyzed Mechanism

摘要

Tautomerism of aldehydes, ketones. and nitroalkanes has played a central role in the development of our ideas about acid-and base-catalyzed reactions. Unlike the interconversion of keto and enol isomers, the nitroalkane nitronic acid prototropy is notacid-catalyzed; this is presumably a consequence of the very poor basicity of the nitro group coupled with its ability to permit C-H cleavage by bases as weak as water itself.