Reactions of aniline with alkali metal diphenylketyls and dianions derived from benzophenone and Michler’s ketone

Abstract

Potassium diphenylketyl and benzophenone dianion react with aniline to afford N-(diphenylmethylene)aniline. Under analogous conditions, the corresponding sodium and lithium derivatives undergo disproportionation with formation of triphenylmethanol, benzoic acid, and diphenylmethanol. The condensation of potassium and sodium bis(4-dimethylaminophenyl)ketyls and salts with Michler's ketone dianion leads to formation of N-[bis(4-dimethylaminophenyl)methylene]aniline, while lithium bis(4-dimethylaminophenyl)ketyl and Michler's ketone dilithium salt are reduced to bis(4-dimethylaminophenyl)methanol.* As in Russian original.-Publisher.

μ2,η1-N-[(N,N-Dimethylamino)dimethylsilyl]-2,6-diisopropylanilido Metal (Li, Zr, Hf) Compounds and the Catalytic Behaviors of the IVB Compounds in Ethylene (Co)Polymerization

“…The reactions of N-substituted anilines with lithium derivatives commonly formed anilidolithium dimers . The potassium hydrido-anilidate, without evidence of crystal structure, was proposed as a reactive intermediate in organic synthesis . Although the acidic properties of the N−H are observed, the stoichiometric reaction of 2,6-diisopropylaniline with n BuLi quantitatively formed the dimeric lithium anilide [LiNH(2,6- i Pr 2 C 6 H 3 )·Et 2 O] 2 ( 1a ), with an isolated yield of 97%.…”