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Silver acetate is a reagent for direct ortho-arylation (to install two adjacent substituents on an aromatic ring) of benzylamines and N-methylbenzylamines.The reaction is palladium-catalyzed and requires a slight excess of silver acetate. [7]
The reaction is named after Cläre Hunsdiecker and her husband Heinz Hunsdiecker, whose work in the 1930s [5] [6] developed it into a general method. [1]The reaction was first demonstrated by Alexander Borodin in 1861 in his reports of the preparation of methyl bromide (CH 3 Br) from silver acetate (CH 3 CO 2 Ag).
Addition of base assists the removal of a proton from acetylacetone and shifts the equilibrium in favour of the complex. Both oxygen centres bind to the metal to form a six-membered chelate ring. In some cases the chelate effect is so strong that no added base is needed to form the complex. Some complexes are prepared by metathesis using Tl(acac).
A molecular monocarboxylate is silver acetate, Ag 2 (OAc) 2. Molecular diacetates are more common. Several diacetates adopt the Chinese lantern structure. Well studied examples include the dimetal tetraacetates (M 2 (OAc) 4) including rhodium(II) acetate, copper(II) acetate, molybdenum(II) acetate, and chromium(II) acetate.
Apart from Leopoldo Nobili, who already in 1824 performed his first experiments related to the appearance of Nobili's rings, Leonhard Elsner, Alexander Watt, Antoine César Becquerel (1788–1878) and Rudolf Christian Böttger (1806–1881) also dealt with the electrochemical coloring of metals in that early period.
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