Chemistry of N2O

Nitrous oxide (N2O) is a highly inert molecule. This dissertation summarizes studies of the chemical activation of nitrous oxide. Our results demonstrate the untapped potential of N2O as a reagent in the synthesis of more complex molecules. N-Heterocyclic carbenes (NHCs) react with nitrous oxide at room temperature to form covalent adducts. Most adducts are stable at room temperature, but heating causes decomposition to the corresponding ureas. Coordination of N2O with NHCs significantly weakens the N-N bond, and facile cleavage of the N-N bond was observed in reactions with acid, methyl iodide, or acetyl chloride. It was shown that NHC-N2O adducts can be converted to azoimidazolium dyes in good to excellent yields. The coordination chemistry of IMes-N2O (IMes = 1,3-dimesitylimidazol-2-ylidene) was studied in reactions with various metal complexes. Structural analysis showed that IMes-N2O can act as an N, O donor or a chelating N, O donor. The reactivity of NHC-N2O adducts toward low-valent metal complexes was also investigated.