Chemische Berichte

Preparation of 3, 4, 5??Trisubstituted 1, 2, 4??Oxadiazolium Salts from Nitrilium Salts

R El??Halawa, PB Dawadi, JC Jochims

Index: Abu-El-Halawa, Rajab; Shrestha-Dawadi, Prativa Bade; Jochims, Johannes C. Chemische Berichte, 1993 , vol. 126, # 1 p. 109 - 116

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Citation Number: 12

Abstract

Abstract 1, 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 ...