An exploding N-isocyanide reagent formally composed of anthracene, dinitrogen and a carbon atom

Abstract

Targeted as an example of a compound composed of a carbon atom together with two stable neutral leaving groups, 7-isocyano-7-azadibenzonorbornadiene, CN₂A (1, A = C₁₄H₁₀ or anthracene) has been synthesized and spectroscopically and structurally characterized. The terminal C atom of 1 can be transferred: mesityl nitrile oxide reacts with 1 to produce carbon monoxide, likely via intermediacy of the N-isocyanate OCN₂A. Reaction of 1 with [RuCl₂(CO)(PCy₃)₂] leads to [RuCl₂(CO)(1)(PCy₃)₂] which decomposes unselectively: in the product mixture, the carbide complex [RuCl₂(C)(PCy₃)₂] was detected. Upon heating in the solid state or in solution, 1 decomposes to A, N₂ and cyanogen (C₂N₂) as substantiated using molecular beam mass spectrometry, IR and NMR spectroscopy techniques.