An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide

Nagatoshi Nishiwaki; Kazuya Kobiro; Hideyuki Kiyoto; Shotaro Hirao; Jun Sawayama; Kazuhiko Saigo; Yoshikazu Okajima; Toshiharu Uehara; Asaka Maki; Masahiro Ariga

doi:10.1039/C0OB01005G

An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide†

Nagatoshi Nishiwaki,*^a Kazuya Kobiro,^a Hideyuki Kiyoto,^a Shotaro Hirao,^a Jun Sawayama,^a Kazuhiko Saigo,^a Yoshikazu Okajima,^b Toshiharu Uehara,^b Asaka Maki^b and Masahiro Ariga^b

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^a School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada Kami, Kochi, Japan
E-mail: nishiwaki.nagatoshi@kochi-tech.ac.jp
Fax: +81 887 57 2520
Tel: +81 887 57 2517

^b Department of Chemistry, Osaka Kyoiku University, Asahigaoka, Kashiwara, Osaka, Japan

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.

Organic & Biomolecular Chemistry

An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide†

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An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide

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