Reaction of Aliphatic Diazo Compounds with Dinitrogen Trioxide. A Facile route to 3,4-Disubstituted 1,2,5-Oxadiazole-2-oxides(Furoxans)

Abstract

As part of our continuing studies¹of the chemistry of diazo compounds, we have investigated the reaction of α-diazosulfones, α-diazoketones and ethyl diazoacetate with dinitrogen trioxide. When a solution of the diazo compound is allowed to react at 0–5° with excess n₂O₃ ² in CH₂Cl₂, and almost instantaneous evolution of a gas (presumably nitrogen) is observed. Work-up afforded 3,4–disubstituted furoxans (I–VII, see Table) in good Yields.