94880-95-2Relevant academic research and scientific papers
Selective and Catalytic Hydrocarboxylation of Enamides and Imines with CO2 to Generate α,α-Disubstituted α-Amino Acids
Ju, Tao,Fu, Qiang,Ye, Jian-Heng,Zhang, Zhen,Liao, Li-Li,Yan, Si-Shun,Tian, Xing-Yang,Luo, Shu-Ping,Li, Jing,Yu, Da-Gang
supporting information, p. 13897 - 13901 (2018/09/27)
The first catalytic hydrocarboxylation of enamides and imines with CO2 to generate valuable α,α-disubstituted α-amino acids is reported. Notably, excellent chemo- and regio-selectivity are achieved, significantly different from previous reports
Studies on the reactivity pattern of in situ generated tetraethylammonium superoxide with 2-oxazolin-5-ones
Singh, Krishna Nand,Kumar, Rajesh
, p. 381 - 386 (2007/10/03)
A variety of 2-oxazolin-5-ones have been allowed to react under the mild reaction conditions of potassium superoxide and tetraethylammonium bromide in dry dimethylformamide at room temperature. Different products are obtained depending on the substituents attached to the C-4 position.
Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide
Buijs, Wim,Comba, Peter,Corneli, Danny,Pritzkow, Hans
, p. 71 - 80 (2007/10/03)
N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L1)(TMAO)2] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L1)2-, coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L=1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction.
Electron transfer reactions. Reaction of Δ2-oxazoline-5-ones and related substrates with potassium
Muneer, Mohammed,Tikare, Ravindra K.,Kamat, Prashant V.,George, Manapurathu V.
, p. 1624 - 1630 (2007/10/02)
The reaction of several Δ2-oxazolin-5-ones (1a-c, 12) and bioxazolinones (17, 26) with potassium in THF has been investigated.Treatment of 1a with potassium in THF gave a mixture of dibenzamide (11a), N-benzoyl-C-phenylglycine (6a), and C-phenylglycine (10a).A higher yield of 11a was obtained, together with benzoic acid (9), when the reaction of 1a wascarried out in THF saturated with oxygen.The reaction of 1b gave a mixture of β-phenylalanine (10b) and 9, whereas 1c gave a mixture of N-benzoyl-C,C-diphenylglycine (6c) and N-benzoyl-C,C-diphenylmethylamine (5c).Similarly, the reaction of 12 gave a mixture of α-benzamidocinnamic ac id (15) and 9.The reaction of the bioxazolinone 17 with potassium gave a mixture of 11a, 6a, and 10a, along with an appreciable yield of 2,3,5,6-tetraphenylpyrazine (25), whereas 26 under analogous conditions gave a mixture of 15, 6b, and benzamide (29).Reasonable mechanisms, involving the initial formation of radical anion intermediates and their subsequent transformation to give the observed products, have been suggested.Potassium superoxide oxidation of some of these substrates gives similar product mixtures.Cyclic voltammetric studies have been carried out to measure the reduction potentials of 1a-c, 12, 17, and 26 in the generation of their radical anions.The radical anions of these substrates were also generated pulse radiolytically in methanol and their spectra showed absorption maxima in the region 295-350 nm.
