title: An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide.
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.
authors.affiliation: School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada Kami, Kochi, 782-8502, Japan. nishiwaki.nagatoshi@kochi-tech.ac.jp
authors.forename: Nagatoshi
authors.initials: N
authors.lastname: Nishiwaki
authors.forename: Kazuya
authors.initials: K
authors.lastname: Kobiro
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Kiyoto
authors.forename: Shotaro
authors.initials: S
authors.lastname: Hirao
authors.forename: Jun
authors.initials: J
authors.lastname: Sawayama
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Saigo
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Okajima
authors.forename: Toshiharu
authors.initials: T
authors.lastname: Uehara
authors.forename: Asaka
authors.initials: A
authors.lastname: Maki
authors.forename: Masahiro
authors.initials: M
authors.lastname: Ariga