Christeena Mathew, Alexandre Genoux, Damien W Chen, Abdusalom A Suleymanov, Farzaneh Fadaei-Tirani, Rosario Scopelliti, Kay Severin
Reactions of organoalkali metal compounds with N2O are generally believed to proceed via diazotate intermediates. Herein, we provide experimental evidence for the formation of diazotates in reactions of Ph2CCPhM (M = Li or K) with N2O, including the crystallographic analysis of [Ph2CCPh(N2O)][K×(18-crown-6)]. Upon the addition of Grignard reagents, the lithium diazotate is converted into azo olefins in synthetically useful yields.