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oai:riubu.ubu.es:10259/42792022-04-29T12:02:48Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

00925njm 22002777a 4500 dc Velasco, Rocío author Silva López, Carlos author Nieto Faza, Olalla . author Sanz Díez, Roberto author 2016-10 By carefullycontrolling the reactiontemperature,treatment of aryl benzylethers with tBuLi selectivelyleadsto a-lithiation, generating stable organolithiums that can bedirectlytrapped with avariety of selected electro philes,before they can undergo the expected [1,2]-Wittigrear-rangement. This rearrangement has been deeplystudied,both experimentally and computationally,with aryl a-lithiat-ed benzyl ethers bearing different substituents at the arylring. The obtained resultssupport the competence of acon-certedanionic intramolecular addition/elimination sequenceand aradical dissociation/recombination sequence for ex-plaining the tendency of migrationfor aryl groups.Themore favored rearrangementsare found for substrates withelectron-poor aryl groups that favor the anionic pathway 0947-6539 http://hdl.handle.net/10259/4279 density functio nal calculations lithiation oxygenheterocycles reaction mechanisms Wittig rearrangement Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited