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 COT(2-) species.