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, CN[subscript 2]A (1, A = C[subscript 14]H[subscript 10] 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 OCN[subscript 2]A. Reaction of 1 with [RuCl[subscript 2](CO)(PCy[subscript 3])[subscript 2]] leads to [RuCl2(CO)(1)(PCy3)2] which decomposes unselectively: in the product mixture, the carbide complex [RuCl[subscript 2[](C)(PCy[subscript 3])[subscript 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.