The Reversibility of the Friedel—Crafts Condensation. The Benzal- and Dibenzal-acetones

Dipole stabilized carbanions. Reactions of benzoate esters with lithium 2,2,6,6-tetramethylpiperidide

“…Two recrystallizations from methanol gave white needles, mp 124-125°, identical in ir, NMR, mass spectrum, melting point, and mixture melting point with authentic dibenzhydrylacetone prepared from dibenzalacetone, benzene, and aluminum trichloride. 24 Vinyl benzoate (12) was allowed to react with LiTMP both at -78 and 25°in either the normal or inverse modes of addition. Analysis by TLC indicated low yields of 13 in both cases.…”

DFT insights into superelectrophilic activation of α,β-unsaturated nitriles and ketones in superacids

“…Superelectrophiles 39 react readily with benzene, affording 4,4-diphenylbutan-2-one after quenching with water. 48,49 When the reaction of 14 with benzene is carried out using proton superacids (TfOH, TfOH–SbF 5 ) 3 or HUSY zeolites, 50 the diprotonated form 5a is obviously the key intermediate.…”

Friedel-Crafts Reaction Involving Unsaturated Ketones and Esters. II. Convenient Syntheses of some Alkylnaphthalenes

“…However, the recent observations of Chaudhuri (7) on the aluminum chloride-catalyzed reaction between toluene and -valerolaetone support our results. Anomalies in the orientation in dior tri-alkylation have been explained on the basis of the reversibility of the Friedel-Crafts alkylation (8). Again, normal alkylation to form the 1,2,4-trialkyl derivative, followed by elimination of the alkyl group at the 1-position was postulated (9) in order to account for the abnormal m-alkylation.…”