Paleo Pillado, María RitaMartínez García, LucasLobato, RubénPrado, GustavoMonje, PabloSardina López, Francisco Javier2024-02-092024-02-092019-01-21Martínez-García, L., Lobato, R., Prado, G., Monje, P., Sardina, F.J., and Paleo, M.R. (2019). C-C bond-forming and bond-breaking processes from the reaction of diesters with Me3SnLi. Synthesis of complex bridged polycycles and di-alkyl aromatic compounds. The Journal of Organic Chemistry, 84 (4), 1887–18970022-3263http://hdl.handle.net/10347/32654This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry (JOC), copyright © American Chemical Society after peer review. To access the final edited and published work see https://doi.org/10.1021/acs.joc.8b02891.1,2-Aromatic diesters can be transformed into strained bridged polycyclic structures by a two-step procedure consisting of an initial reductive alkylation promoted by alkaline metals, followed by a reaction of the resulting unsaturated diesters with Me3SnLi. We propose that a stanna-Brook rearrangement plays a fundamental role in the formation of the polycyclic organotin acetals obtained. These unusual compounds could be further functionalized by tin–lithium exchange followed by alkylation of the newly formed tertiary carbanion. Alternatively, dialkylated aromatic hydrocarbons have been prepared via a decarbonilation reaction promoted by Me3SnLi. 1,4-Aromatic diesters were reductively dialkylated and then transformed into norbornadienone derivatives by reaction with Me3SnLi. Several stable dibenzonorbornadienones 41 have been prepared in just two steps starting from anthracene 38. The corresponding naphthalene analogues gave 1,4-dialkylnaphthalenes. The synthetic protocols described provide access to structures that are not easily obtained through existing synthetic methodologies.engCopyright © 2019 American Chemical Society. Non-commercial purposes.http://creativecommons.org/licenses/by-nc-nd/4.0/Aromatic compoundsChemical reactionsHydrocarbonsReaction products2306 Química orgánica230602 Hidrocarburos aromáticos230615 Mecanismos de reacciónjournal article10.1021/acs.joc.8b028911520-6904open access