Photolysis of each of the prepared N-haloamide complexes in the presence of weak C-H bond donors, such as THF, results in formal nitrene transfer chemistry. Given previous demonstrations of C-H amination via amidyl radical intermediates, the observation of amination products is insufficient to differentiate between the potential photogeneration of a highvalent nitrenoid or N-centered radical intermediates. Halogen-dependent photochemistry is observed with other substrates that are commonly encountered in nitrene transfer chemistry.