Reactions of 2,2‐dimethylaziridine with benzohydroximoyl chlorides [ArC(Cl)NOH] give aziridinylbenzaldoximes 1. It has been found that the aziridine ring in these compounds undergoes ring opening in hydrogen chloride‐dioxane solution to give (Z)‐N‐hydroxy‐N′‐(2‐chloro‐2‐methylpropyl)benzenecarboximidamides [ArC(NHCH2CR1R2Cl)NOH, 4]. Treatment of 1 with hydrochloric acid followed by neutralization with aqueous sodium hydroxide gave 6,6‐dimethyl‐3‐aryl‐1,2,4‐oxadiazines 2. Reaction of 4 with sodium hydride in dioxane gave 5‐isopropyl‐3‐aryl‐4,5‐dihydro‐1,2,4‐oxadiazoles 5. Reaction of the 4,5‐dihydro‐1,2,4‐oxadiazoles 5 with N‐chlorosuccinimide gave the heteroaromatic 1,2,4‐oxadiazoles 6. It is suggested that reactions of 4 with sodium hydride in dioxane solution involve the conjugate base of 4 which undergoes a 1,2‐hydride shift that is concerted with loss of chloride ion. In aqueous sodium hydroxide solution it is suggested that the conjugate base of 4 undergoes ionization of the chlorine atom followed by nucleophilic attack by the oximate anion.
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