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1,2-Bis(diphenylphosphino)ethylene

1,2-Bis(diphenylphosphino)ethylene, often abbreviated as dppe, is an organophosphorus compound used extensively as a bidentate phosphine ligand in coordination chemistry and homogeneous catalysis. It consists of an ethylene backbone with two diphenylphosphine (PPh2) groups attached to adjacent carbon atoms.

Dppe is a solid at room temperature and is typically air-stable, although it is best stored under an inert atmosphere to prevent slow oxidation of the phosphorus atoms. It is soluble in common organic solvents like dichloromethane, tetrahydrofuran, and toluene.

As a ligand, dppe forms stable complexes with a wide range of transition metals. Its chelating nature, owing to the two phosphorus atoms coordinating to the same metal center, contributes to the enhanced stability of these complexes. The ethylene bridge between the phosphine groups gives dppe a relatively small bite angle (the P-M-P angle), which can influence the reactivity and selectivity of the resulting metal complexes. This property makes it useful in designing catalysts for various chemical reactions, including hydrogenation, hydroformylation, and cross-coupling reactions. The ligand's steric bulk provided by the phenyl groups also plays a role in influencing the catalytic activity and selectivity.

Dppe is typically synthesized by reacting 1,2-dichloroethane with lithium diphenylphosphide. The phosphide reagent displaces the chloride atoms, resulting in the formation of the desired dppe product.