Abstract
This review article summarizes efforts to use nitrous oxide (N2O, 'laughing gas') as a reagent in synthetic chemistry. The focus will be on reactions which are carried out in homogeneous solution under (relatively) mild conditions. First, the utilization of N2O as an oxidant is discussed. Due to the low intrinsic reactivity of N2O, selective oxidation reactions of highly reactive compounds are possible. Furthermore, it is shown that transition metal complexes can be used to catalyze oxidation reactions, in some cases with high turnover numbers. In the final part of this overview, the utilization of N2O as a building block for more complex molecules is discussed. It is shown that N2O can be used as an N-atom donor for the synthesis of interesting organic molecules such as triazenes and azo dyes.
Highlights
Since its discovery in 1772 by Joseph Priestley, nitrous oxide has had a remarkable career.[1]
It is shown that transition metal complexes can be used to catalyze oxidation reactions, in some cases with high turnover numbers
Reaction of transition metal complexes with N2O are hampered by the fact that N2O is a very poor ligand.[10]
Summary
Since its discovery in 1772 by Joseph Priestley, nitrous oxide has had a remarkable career.[1]. In the second part of the 19th century, N2O was employed as an anesthetic by dentists This application is less common today, but in some countries, N2O is given as a pain relief during childbirth.[2] Very preliminary results indicate that N2O could be used as a drug for patients with treatment-resistant depression.[3] More technical applications include its utilization as a whipping agent for cream or as a fuel additive for rockets and motors.[1] But there is a ‘dark side’ of N2O, and that is its environmental impact. The utilization of high pressure and temperature in combination with heterogeneous catalysts allows performing oxidation reactions with N2O. These kinds of reactions have been summarized before,[9] and they are not discussed in this. For a description of the ligand properties of N2O, the reader is referred to an excellent review article by Tolman.[10]
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