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Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%) [10] [11] The methanol formed is recycled in the process of oxidative carbonylation. [12] Other plants with a total annual capacity of more than 1 million tons of ethylene glycol per year are planned. Decarbonylation gives dimethyl carbonate. [13]
Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula C 2 O 2− 4. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na 2 C 2 O 4), and several esters such as dimethyl oxalate ((CH 3) 2 C 2 O 4). It is a conjugate base of oxalic acid.
Diisopropylamine is a common amine nucleophile in organic synthesis. [4] Because it is bulky, it is a more selective nucleophile than other similar amines, such as dimethylamine. [5] It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base [6]
Transition metal oxalate complexes are coordination complexes with oxalate (C 2 O 4 2−) ligands. Some are useful commercially, but the topic has attracted regular scholarly scrutiny. Oxalate (C 2 O 4 2-) is a kind of dicarboxylate ligand. [1] As a small, symmetrical dinegative ion, oxalate commonly forms five-membered MO 2 C 2 chelate rings.
Oxalyl chloride reacts with water giving off gaseous products only: hydrogen chloride (HCl), carbon dioxide (CO 2), and carbon monoxide (CO). (COCl) 2 + H 2 O → 2 HCl + CO 2 + CO In this, it is quite different from other acyl chlorides which hydrolyze with formation of hydrogen chloride and the original carboxylic acid.
Azathioprine is synthesized from 5-chloro-1-methyl-4-nitro-1H-imidazole and 6-mercaptopurine in dimethyl sulfoxide. [73] The synthesis of the former starts with an amide from methylamine and diethyl oxalate, which is then cyclized and chlorinated with phosphorus pentachloride; [74] the nitro group is introduced with nitric and sulfuric acid.
The first step of the synthesis is the condensation of o-nitrotoluene 1 with a diethyl oxalate 2 to give ethyl o-nitrophenylpyruvate 3. The reductive cyclization of 3 with zinc in acetic acid gives indole-2-carboxylic acid 4. If desired, 4 can be decarboxylated with heat to give indole 5.
The Sharpless epoxidation is viable with a large range of primary and secondary alkenic alcohols. Furthermore, with the exception noted above, a given dialkyl tartrate will preferentially add to the same face independent of the substitution on the alkene.To demonstrate the synthetic utility of the Sharpless epoxidation, the Sharpless group created synthetic intermediates of various natural ...