000127006 001__ 127006
000127006 005__ 20241125101151.0
000127006 0247_ $$2doi$$a10.1016/j.tet.2023.133450
000127006 0248_ $$2sideral$$a133877
000127006 037__ $$aART-2023-133877
000127006 041__ $$aeng
000127006 100__ $$aDorado, V.
000127006 245__ $$aSimple metal-free oxidative cleavage of 1,2-diols
000127006 260__ $$c2023
000127006 5060_ $$aAccess copy available to the general public$$fUnrestricted
000127006 5203_ $$aCleavage of 1,2-diols is easily carried out under mild conditions with the Oxone/KBr (or Oxone/NaCl) method in either acetonitrile/water or tert-butanol/water medium at room temperature. This procedure is highly efficient for the cleavage of dihydroxyfatty esters and acids. The reaction takes place through a double oxidation of the 1,2-diol, leading to the 1,2-diketone that undergoes a Baeyer-Villiger oxidation, with a final hydrolysis of the generated anhydride. The application to other diols, including simple internal and terminal diols, is also possible, but the nature of the diol substrate conditions the optimal halide/solvent system, given that important differences in reactivity are observed. These differences are ascribed to the change in the rate limiting step depending on the substrate/halide/solvent combination
000127006 536__ $$9info:eu-repo/grantAgreement/ES/DGA-ERDF/E37-20R$$9info:eu-repo/grantAgreement/ES/MICINN/RTI2018-093431-B-100$$9info:eu-repo/grantAgreement/ES/MINECO/PID2021-125762NB-I00
000127006 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000127006 590__ $$a2.1$$b2023
000127006 592__ $$a0.406$$b2023
000127006 591__ $$aCHEMISTRY, ORGANIC$$b24 / 58 = 0.414$$c2023$$dQ2$$eT2
000127006 593__ $$aBiochemistry$$c2023$$dQ3
000127006 593__ $$aOrganic Chemistry$$c2023$$dQ3
000127006 593__ $$aDrug Discovery$$c2023$$dQ3
000127006 594__ $$a3.9$$b2023
000127006 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000127006 700__ $$0(orcid)0000-0002-7272-8506$$aHerrerías, C. I.$$uUniversidad de Zaragoza
000127006 700__ $$0(orcid)0000-0002-0136-5138$$aFraile, J. M.
000127006 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000127006 773__ $$g139 (2023), 133450 [7 pp.]$$pTetrahedron$$tTETRAHEDRON$$x0040-4020
000127006 8564_ $$s605694$$uhttps://zaguan.unizar.es/record/127006/files/texto_completo.pdf$$yVersión publicada
000127006 8564_ $$s2762657$$uhttps://zaguan.unizar.es/record/127006/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000127006 909CO $$ooai:zaguan.unizar.es:127006$$particulos$$pdriver
000127006 951__ $$a2024-11-22-12:07:01
000127006 980__ $$aARTICLE