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