1,2-Bis(diphenylphosphino)ethane

1,2-Bis(diphenylphosphino)ethane (dppe) is a commonly used bidentate ligand in coordination chemistry. Dppe is almost invariably chelating, although there are some rare examples of monodentate (only one P-atom attached) complexes.

Structure and Bonding

1,2-Bis(diphenylphosphino)ethane is a white, crystalline solid that is soluble in organic solvents. It is a strong reducing agent and can reduce a variety of organic and inorganic compounds. The molecule consists of a two-carbon alkane backbone with a phenyl group and a phosphine substituent on each carbon. The phosphine groups are able to donate electron density to a metal center, forming a coordinate covalent bond.

Synthesis

1,2-Bis(diphenylphosphino)ethane can be synthesized by the reaction of chlorodiphenylphosphine with sodium ethoxide in ethanol. The reaction proceeds via a nucleophilic substitution mechanism, with the sodium ethoxide acting as the nucleophile.

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Applications

1,2-Bis(diphenylphosphino)ethane is used as a ligand in the synthesis of a variety of metal complexes, including those of transition metals such as palladium, platinum, and nickel. These complexes have applications in catalysis, including hydrogenation, carbon-carbon bond formation, and cross-coupling reactions.

Safety

1,2-Bis(diphenylphosphino)ethane is harmful if swallowed, inhaled, or comes into contact with skin. It is also harmful to aquatic life. Proper personal protective equipment should be used when handling this compound.

See also

• Phosphine ligand
• Transition metal phosphine complex
• Cross-coupling reaction