Abstract
Alkali matals form complexes with cyclic polyethers in etheric solvents to generate alkali metal anions. In toluene as solvent, one electron transfer from these metal anions to the solvent results in production of the toluene radical anion.Both of these chemical species exert unique ability of reducing various kinds of functional groups. For example, the former system (K/dicyclohexano-18-crown-6/diglyme) is effective for cleavage of O-sulfonate or sulfonamide, and also for reduction of a certain type of unsaturated carbon-carbon bonds. On the other hand, the latter system (K/dicyclohexano-18-crown-6/toluene) reductively cleaves various types of unactivated aliphatic carbon-fluorine or carbon-nitrile bonds in almost quantitative fashion.
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