@ARTICLE{Velasco201615058,
author={Velasco, R. and Silva López, C. and Nieto Faza, O. and Sanz, R.},
title={Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited},
journal={Chemistry - A European Journal},
year={2016},
volume={22},
number={42},
pages={15058-15068},
doi={10.1002/chem.201602254},
abstract={By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to α-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl α-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim},
}

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