1936
DOI: 10.1021/ja01297a017
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The Oxidation of Amino Acids with Sodium Hypobromite

Abstract: 150°and 145-147°, respectively. In ether these iodides decompose slowly with the liberation of iodine.Optical Properties.-Indium trimethylsulfonium chloride crystallized in such irregularly twinned monoclinic prisms that the refractive indices could not be determined. Indium trimethyl sulfonium iodide yielded anisotropic crystals whose indices of refraction were greater than that of methylene iodide. Indium triethylsulfonium iodide gave such extremely minute crystals that the optical properties could not be de… Show more

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Cited by 37 publications
(29 citation statements)
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“…By analogy with what is known for enzyme- [16a] and NaOBr-mediated oxidative decarboxylation, [20] a mech-anism can be proposed (Scheme 1). First, an N-bromo amino acid derivative is formed, which reacts further through two parallel pathways.…”
Section: Resultsmentioning
confidence: 96%
“…By analogy with what is known for enzyme- [16a] and NaOBr-mediated oxidative decarboxylation, [20] a mech-anism can be proposed (Scheme 1). First, an N-bromo amino acid derivative is formed, which reacts further through two parallel pathways.…”
Section: Resultsmentioning
confidence: 96%
“…Routes for chemical or enzymatic decarboxylation of amino acids have been studied in the past 414. Chemical methods use stoichiometric oxidants such as sodium hypohalites,46 N ‐bromosuccinimide,7,10 1‐chlorobenzotriazole,9 trichloroisocyanuric acid,10 and 2‐iodoxybenzoic acid 12. These oxidants supply the halonium species that effect the oxidative decarboxylation on the α‐carbon atom.…”
Section: Introductionmentioning
confidence: 99%
“…An intermediate imine generates the carbonyl product through hydrolysis, as shown in eqs. (2) and (3).…”
Section: Rch(nhc1)cooh + Ho --+ Rchomentioning
confidence: 99%
“…Several mechanisms have been proposed, but for the reaction shown as eq. (2), opinion seems to have converged on a concerted unimolecular decomposition with a delocalized transition state shown as structure I [5-lo]. …”
Section: Rch(nhc1)coo-mentioning
confidence: 99%