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The Buchner ring expansion reaction was first used in 1885 by Eduard Buchner and Theodor Curtius [1] [2] who prepared a carbene from ethyl diazoacetate for addition to benzene using both thermal and photochemical pathways in the synthesis of cycloheptatriene derivatives. The resulting product was a mixture of four isomeric carboxylic acids ...
Decarbonylation can be catalyzed by soluble metal complexes. [6] [5] These reactions proceed via the intermediacy of metal acyl hydrides. An example of this is the Tsuji–Wilkinson decarbonylation reaction using Wilkinson's catalyst. (Strictly speaking, the noncatalytic version of this reaction results in the formation of a rhodium carbonyl ...
The first reported decarboxylative cross coupling reaction was an Ullmann reaction, in 1966 by Nilsson et al. Thermal decarboxylation of copper benzoates, in the presence of an aryl halide, was found to produce (both symmetric and unsymmetric) biaryls through aryl-Cu intermediates. [2] First reported decarboxylative Ullmann coupling (Nilsson, 2005)
Transition metal salts, especially copper compounds, [9] facilitate decarboxylation via carboxylate complex intermediates. Metals that catalyze cross-coupling reactions thus treat aryl carboxylates as an aryl anion synthon; this synthetic strategy is the decarboxylative cross-coupling reaction. [10] Upon heating in cyclohexanone, amino acids ...
Using a carboxylate-to-iodine ratio of 1:1 leads to an alkyl iodide product, in line with Borodin's findings and the modern understanding of the Hunsdiecker reaction. However, a 2:1 ratio favours the formation of an ester product that arises from decarboxylation of one carboxylate and coupling the resulting alkyl chain with the other. [9] [10]
The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product. [1] [2] This is
1,2-Bis(dimethylarsino)benzene (diars) is the organoarsenic compound with the formula C 6 H 4 (As(CH 3) 2) 2. The molecule consists of two dimethylarsino groups attached to adjacent carbon centers of a benzene ring. It is a chelating ligand in coordination chemistry. This colourless oil is commonly abbreviated "diars." [1]
Phenol and halobenzenes can be reduced with metals. Benzoic acid and its salts undergo decarboxylation to benzene. ... to 63 to 405 mg/m 3 of benzene for 1 to 5 hours ...