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Reactivity of a Sodium Anion with Alkenes: 1-Electron vs 2-Electron Reductions

Lookup NU author(s): Huanxin Zhang, Dr Nathan Davison, Dr Jack Hemingway, Dr Paul Waddell, Dr James DawsonORCiD, Dr Erli Lu

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).


Abstract

© 2025 The Authors. Published by American Chemical Society. The sodium anion (sodide) is an uncommon alkali metal species, whose reactivity has been scarcely studied, with previous reports limited to decomposition and quenching reactions of ill-characterized species formed in situ. Based on our recent report of the first gram-scale synthesis of a well-characterized sodide complex, [Na+(2,2,2-cryptand)]Na– (1), we now describe its reactivity with phenyl-substituted ethylenes and a cyclic polyolefin. Depending on the substitution pattern, 1 mediates either 1-electron or 2-electron reduction. Reaction with a cyclic multiolefin, 1,3,5,7-cyclooctatetraene (COT), exhibits two-electron reduction to produce COT2– species.


Publication metadata

Author(s): Zhang H, Davison N, Hemingway JM, Male L, Waddell PG, Deakin J, Tuna F, Dawson JA, Lu E

Publication type: Article

Publication status: Published

Journal: Inorganic Chemistry

Year: 2025

Volume: 64

Issue: 51

Pages: 25195-25204

Print publication date: 29/12/2025

Online publication date: 12/12/2025

Acceptance date: 03/12/2025

Date deposited: 12/01/2026

ISSN (print): 0020-1669

ISSN (electronic): 1520-510X

Publisher: American Chemical Society

URL: https://doi.org/10.1021/acs.inorgchem.5c04279

DOI: 10.1021/acs.inorgchem.5c04279

Data Access Statement: The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.inorgchem.5c04279.

PubMed id: 41383120


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Funding

Funder referenceFunder name
Leverhulme Trust, Research Grant projects RPG-2023-159 and RPG-2022-231
University of Birmingham

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