Thermal decomposition of meso- and d,l-3,4-diethyl-3,4-dimethyldiazetine N,N'-dioxide.

Two stereochemically defined diazetine N,N'-dioxides were synthesized. Thermal decomposition at 200 degrees C resulted in 95% retention of stereochemistry in the alkene product relative to the starting stereochemistry. These results suggest that decomposition occurs via cleavage of the two C-N bonds either simultaneously or in rapid succession.