@article{oai:kutarr.kochi-tech.ac.jp:00000224, author = {Nishiwaki, Nagatoshi and Kobiro, Kazuya and Kiyoto, Hideyuki and Hirao, Shotaro and Sawayama, Jun and Saigo, Kazuhiko and Okajima, Yoshikazu and Uehara, Toshiharu and Maki, Asaka and Ariga, Masahiro}, issue = {8}, journal = {Organic & Biomolecular Chemistry}, month = {}, note = {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.}, pages = {2832--2839}, title = {An anomalous hydration/dehydration sequence for the mild generation of a nitrile oxide}, volume = {9}, year = {2011} }