ChemInform Abstract: An Anomalous Hydration/Dehydration Sequence for the Mild Generation of a Nitrile Oxide.

Abstract

An Anomalous Hydration/Dehydration Sequence for the Mild Generation of a Nitrile Oxide. -Treatment of isoxazolinones (I) with water under mild conditions generates a nitrile oxide (VI) which smoothly undergoes cycloaddition with various dipolarophiles furnishing isoxazoles (III) and isoxazolines (V). A plausible reaction mechanism is proposed. -(NISHIWAKI*, N.; KOBIRO, K.; KIYOTO, H.; HIRAO, S.; SAWAYAMA, J.; SAIGO, K.; OKAJIMA, Y.; UEHARA, T.; MAKI, A.; ARIGA, M.; Org. Biomol. Chem. 9 (2011) 8, 2832-2839, http://dx.doi.org/10.1039/c0ob01005g ; Sch. Environ. Sci. Eng., Kochi Univ. Technol., Kami, Kochi 782, Japan; Eng.) -Mischke 33-109