Catalytic Activation of CH Bonds in Aromatic Hydrocarbons, Ethene, and Methane by the Naphthalene/Sodium System in Tetrahydrofuran

Remarkable news concerning the long‐known and well‐investigated reaction system naphthalene/sodium in THF is reported: At room temperature a reversible intermolecular transfer of hydrogen takes place both between naphthalene rings and also with THF molecules. In contrast, the corresponding lithium and potassium systems show no such behavior. In addition, alkanes and cycloalkanes as solvent additives effect a significant increase in the H/D exchange rate in the sodium system. Benzene, toluene, ethene, and even methane (!) also take part in the H/D exchange reactions in the naphthalene/sodium system.