Woollins' reagent

It can also be conveniently prepared in the laboratory by heating a mixture of dichlorophenylphosphine and sodium selenide (Na2Se), (itself prepared from reacting elementary selenium with sodium in liquid ammonia).

[2] An alternative synthesis is the reaction of the pentamer (PPh)5 (pentaphenylcyclopentaphosphine) with elemental selenium.

[3] The main use of Woollins' reagent is the selenation of carbonyl compounds.

[4] For instance, Woollins' reagent will convert a carbonyl into a selenocarbonyl.

Additionally, Woollins' reagent has been used to selenonate carboxylic acids, alkenes, alkynes, and nitriles.

Skeletal formula of Woollins' reagent
3D model of the Woollins' reagent molecule