Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions

The difference in the HOMO–LUMO gap for phenyl and triazolyl diazoacetates is reflected in their reactivity under light irradiation. While photochemical reactions for phenyl diazoacetates can be performed in DCM, triazolyl diazoacetates react with the solvent and become chlorinated. All alkyl halides studied behave in the same way. With other commonly used solvents, C–H or X–H insertions occur. The solvent that allows reactions with other reagents is dimethyl decarbonate.