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

## TL;DR

This paper studies the reactivity of a sodium anion with alkenes, revealing how it can perform one or two-electron reductions depending on the molecule's structure.

## Contribution

The paper reports the first detailed study of a well-characterized sodium anion's reactivity with alkenes and polyolefins.

## Key findings

- The sodium anion mediates 1-electron or 2-electron reductions depending on the substitution pattern of the alkene.
- Reaction with cyclooctatetraene leads to two-electron reduction forming a COT2– species.

## 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+(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.