Dialkyl azodiformates form dihydrooxadiazines with indene, dihydro-1,4-dioxine, vinylene carbonate, cisand irons-1,2-dimethoxyethylene, and vinyl acetate by 1,4 addition; 1,2 addition yielding diazetidines is observed with vinyl ethers. Diazetidines also result from the addition of 4-phenyl-A'-1,2,4-triazoline-3,5-dione (PTD) to indene and dihydro-1,4-dioxine. Dihydrooxadiazines are formed in a concerted Diels-Alder reaction with inverse electron demand, the diazetidines via dipolar intermediates. The acceleration of azodiformate addition by illumination is due to the photochemical production of as azodiformates, which show increased thermal reaction rates compared with the irons isomers.
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