RT info:eu-repo/semantics/article
T1 Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited
A1 Velasco, Rocío
A1 Silva López, Carlos
A1 Nieto Faza, Olalla .
A1 Sanz Díez, Roberto
K1 density functio nal calculations
K1 lithiation
K1 oxygenheterocycles
K1 reaction mechanisms
K1 Wittig rearrangement
K1 Chemistry, Organic
K1 Química orgánica
AB 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
PB Wiley-VCH Verlag
SN 0947-6539
YR 2016
FD 2016-10
LK http://hdl.handle.net/10259/4279
UL http://hdl.handle.net/10259/4279
LA eng
NO Junta de Castilla yLejnandFEDER (BU237U13 and BU076U16) and Ministerio de Econom&ayCompetitividad (MINECO) and FEDER (CTQ2013-48937-C2-1Pand 2-P)
DS Repositorio Institucional de la Universidad de Burgos
RD 29-abr-2024