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Updated: Jun 4, 2026

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
Published on: April 24, 2018
An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide
Nagatoshi Nishiwaki1, Kazuya Kobiro, Hideyuki Kiyoto
1School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada Kami, Kochi, 782-8502, Japan. nishiwaki.nagatoshi@kochi-tech.ac.jp
Abstract:
A nitrile oxide containing a carbamoyl group is readily generated upon the treatment of 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with water under mild reaction conditions, even in the absence of special reagents. The obtained nitrile oxide undergoes cycloaddition with dipolarophiles, alkynes and alkenes, to afford the corresponding isoxazol(in)es, which are useful intermediates in the synthesis of polyfunctionalized compounds. A plausible mechanism underlying the formation of the nitrile oxide is proposed, which involves an anomalous hydration/dehydration sequence. DFT calculations were also performed to support this mechanism.
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