Abstract 5-Methylisoxazoles with electron-accepting groups at C-4 (1a-c) and 2, 3- dimethylisoxazolium iodide (II) undergo ring cleavage when treated with organic bases. The nature of the open chain products which were obtained (stable enolates, β-diketones, esters) depends on the group at C-4 and the strength of the base. In some of these processes aromatic aldehydes were used in order to determine the competition between ...