σ-Anionic complexes of 1,3,5-trinitrobenzene with R3E groups (E = Si, Ge, Sn; R = Me, Et, Ph) and the routes of their transformations

Abstract Anionic σ-complexes, [TNB - ER 3 ] - M + , were obtained by the reaction of 1,3,5-trinitrobenzene (TNB) with R 3 EM (E = Si, Ge, Sn; R = Me, Et, Ph; M = Li, K). Their reactions with CH, NH and OH acids, CBr 4 and N -bromosuccinimide were studied. The mechanism of these transformations was proposed. It was found that in the reaction of Me 3 SnM with 2,4,6-trinitroanisole the latter acts as an alkylating agent, it also exhibits this property towards the other nucleophiles. σ-Complexes [TNB - ER 3 ] - M + , where M = K, Cs, in solution undergo irreversible rearrangement into the metal 3,5-dinitrophenolates. The mechanism for such processes and reactions of R 3 SnM with nitroaromatic compounds in general, are discussed.