Reactions of Grignard Reagents with Nitrous Oxide

The chemical activation of nitrous oxide (N2O) can be achieved by organocalcium, organosodium, and organolithium compounds. Grignard reagents, on the other hand, are believed to be inert. We demonstrate that this generalization is not correct. Some aliphatic Grignard reagents undergo a rapid conversion when subjected to an atmosphere of N2O. Hydrazones are the main reaction products.