Meisenheimer-Wheland complexes between 1,3,5-tris(N,N-dialkylamino)benzenes and 4,6-dinitrotetrazolo[1,5-a]pyridine. Evidence of reversible C-C coupling in the [S.sub.E]Ar/[S.sub.N]Ar reaction

The reactions between a superelectrophilic carbon reagent, 4,6-dinitrotetrazolopyridine, and 1,3,5-tris(N,N-dialkylamino)benzenes, a supernucleophilic carbon reagent series, has afforded C-C coupling products that are edouble [sigma]-complexesE (W-M), Wheland-like on the 1,3,5-tris (N,N-dialkylamino)benzene moiety and Meisenheimer-like on the 4,6-dinitrotetrazolopyridine moiety. The experiments at variable temperature have shown that the formation of these complexes by a nucleophile/electrophile attack is a reversible process.