Abstract
Abstract1,3‐Cycloadditions of stable nitrile oxides 2 to nitrilium salts 1 afford high yields of 3,4,5‐trisubstituted 1,2,4‐oxadiazolium salts 3. N‐Hydroxycarboximidoyl chlorides 4 add to nitrilium salts 1 to give isolable [(chloroalkylidene)aminooxyalkylidene]ammonium salts 5. A thermal stereomutation around the C = N+ bond is observed. On heating neat or in solution most compounds 5 cyclize to oxadiazolium salts 3. In cases where decomposition of 5 is faster than cyclization O‐silylated N‐hydroxycarboximidoyl chlorides 7 are treated with nitrilium salts 1 to furnish oxadiazolium salts 3.
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