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The photochemistry of some 1,2,4-oxadiazoles containing a double bond at the side chain has been investigated. The irradiation yielded different 2-N-benzoylamino-2-oxazoline derivatives depending on the employed reaction solvent (DCM or THF). Photorearrangements occur through an intramolecular aziridination reaction yielding a bicyclic intermediate, which was subjected to in situ aziridine ring opening. Photoinduced addition of HCl, involving the chlorinated solvent as a reagent, gave the corresponding chlorinated 2-oxazoline. In THF, reductive aziridine ring opening was observed.

Solvent dependent photochemical reactivity of 3-allyloxy-1,2,4-oxadiazoles