000060962 001__ 60962
000060962 005__ 20190709135522.0
000060962 0247_ $$2doi$$a10.1039/C7RA01017F
000060962 0248_ $$2sideral$$a98402
000060962 037__ $$aART-2017-98402
000060962 041__ $$aeng
000060962 100__ $$aAngulo, Beatriz
000060962 245__ $$aChallenging cyclopropanation reactions on non-activated double bonds of fatty acids
000060962 260__ $$c2017
000060962 5060_ $$aAccess copy available to the general public$$fUnrestricted
000060962 5203_ $$aMonounsaturated fatty esters with non-activated double bonds have been made to react with two different diazocompounds, ethyl diazoacetate (EDA) and dimethyl diazomalonate (DDM), in copper and rhodium catalyzed cyclopropanation reactions. The corresponding cyclopropanes have been obtained with quantitative or nearly quantitative yields (>99%) in all the cases, with only the exception of the reaction of methyl elaidate, an E alkene, with the less reactive DDM. For the first time, the two stereoisomers of ethyl (2R*,3S*)-2-(7-methoxycarbonyl)heptyl-3-octylcyclopropane-1-carboxylate, obtained from the reaction of methyl oleate and EDA, have been separated and fully characterized. Finally, the diesters and triesters with cyclopropane structure have been reduced to diols and triols, and hydrolyzed to the corresponding diacids and triacids, to demonstrate the potential usefulness of this methodology to prepare monomers from renewable sources.
000060962 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E11$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-52367-R
000060962 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000060962 590__ $$a2.936$$b2017
000060962 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b71 / 171 = 0.415$$c2017$$dQ2$$eT2
000060962 592__ $$a0.863$$b2017
000060962 593__ $$aChemistry (miscellaneous)$$c2017$$dQ1
000060962 593__ $$aChemical Engineering (miscellaneous)$$c2017$$dQ1
000060962 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000060962 700__ $$0(orcid)0000-0002-0136-5138$$aFraile, José Martía$$uUniversidad de Zaragoza
000060962 700__ $$0(orcid)0000-0002-7272-8506$$aHerrerias, Clara Isabel$$uUniversidad de Zaragoza
000060962 700__ $$0(orcid)0000-0003-1570-4257$$aMayoral Murillo, José Antonio$$uUniversidad de Zaragoza
000060962 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000060962 773__ $$g7, 32 (2017), 19417-19424$$pRSC ADVANCES$$tRSC Advances$$x2046-2069
000060962 8564_ $$s588428$$uhttps://zaguan.unizar.es/record/60962/files/texto_completo.pdf$$yVersión publicada
000060962 8564_ $$s123923$$uhttps://zaguan.unizar.es/record/60962/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000060962 909CO $$ooai:zaguan.unizar.es:60962$$particulos$$pdriver
000060962 951__ $$a2019-07-09-11:58:01
000060962 980__ $$aARTICLE