Chemistry of diazocarbonyl compounds: XXVII. Thermolysis and photolysis of diazirines, derivatives of 1,3-dioxane-4,6-dione

Photolysis of diazirines, 1,3-dioxane-4,6-dione derivatives, occurs in the presence of methanol or dimethyl sulfide as carbene traps without a formation of carbene intermediates. It was established for the first time that the thermolysis and photolysis of diazirines from the 1,3-dioxane-4,6-dione series led mainly to Wolff rearrangement with a subsequent formation of 5-oxo-1,3-dioxolane-4-carboxylic acids or their derivatives. The data obtained show that the α-oxodiazirines are the key intermediates in the photolysis and Wolff rearrangement of α-diazocarbonyl compounds.