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The photoaddition of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (4‐MTAD) with a wide variety of acyclic, cyclic and crown aliphatic ethers has been investigated. Monochromatic (λ = 514.5 nm) or polychromatic (λ ≥ 310 nm) irradiations give identical mono‐urazolyl ethers as reaction products. Unsymmetrical acyclic ethers afford a mixture of the two α and α′ mono‐urazolyl ethers. In the case of 12‐crown‐4, mono and di‐substituted products are obtained. ESR experiments and quantum calculations at the AM1 and 6‐31G* levels were performed and a possible reaction mechanism is proposed in which the most probable photochemical process is the H‐abstraction leading to a urazolyl radical.

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