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

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<sup>+</sup>(2,2,2-cryptand)]Na<sup>-</sup> (<b>1</b>), we now describe its reactivity with phenyl-substituted ethylenes and a cyclic polyolefin. Depending on the substitution pattern, <b>1</b> 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 COT<sup>2-</sup> species.

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Journal
Inorganic Chemistry
Published
2025-12-12
DOI
https://doi.org/10.1021/acs.inorgchem.5c04279
Primary Topic
Organometallic Complex Synthesis and Catalysis
Type
article
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article

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

Louise Male, Jack M. Hemingway, James A. Dawson, Floriana Tuna et al.
Inorganic Chemistry
Organometallic Complex Synthesis and Catalysis
article

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

Louise Male, Jack M. Hemingway, James A. Dawson, Floriana Tuna, Huanxin Zhang, Nathan Davison, Erli Lu, Paul Gordon Waddell, Joshua Deakin
article en

Abstract

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<sup>+</sup>(2,2,2-cryptand)]Na<sup>-</sup> (<b>1</b>), we now describe its reactivity with phenyl-substituted ethylenes and a cyclic polyolefin. Depending on the substitution pattern, <b>1</b> 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 COT<sup>2-</sup> species.

Inorganic ChemistryVol. 64(51)
University of Manchester (GB), University of Birmingham (GB), Newcastle University (GB)
Openalex Percentile: Top 70%
Organometallic Complex Synthesis and Catalysis
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Reactivity of a Sodium Anion with Alkenes: 1-Electron vs 2-Electron Reductions — Louise Male, Jack M. Hemingway, et al. · Inorganic Chemistry (2025) | TGRS Research Map | TGRS