Woollins' reagent

Woollins' Reagent

Skeletal formula of Woollins' reagent
3D model of the Woollins' reagent molecule
Names
IUPAC names 2,4-Diphenyl-1,3,2,4- diselenadiphosphetan-2,4-diselenide
Other names Woollins' Reagent
Identifiers
CAS Number	122039-27-4
ChemSpider	4242993
Jmol 3D model	Interactive image
PubChem	5066075
InChI InChI=1S/C12H10P2Se4/c15-13(11-7-3-1-4-8-11)17-14(16,18-13)12-9-5-2-6-10-12/h1-10H Key: GKYFQRQKPYPLGJ-UHFFFAOYSA-N InChI=1/C12H10P2Se4/c15-13(11-7-3-1-4-8-11)17-14(16,18-13)12-9-5-2-6-10-12/h1-10H Key: GKYFQRQKPYPLGJ-UHFFFAOYAX
SMILES C1=CC=C(C=C1)P2(=[Se])[Se]P(=[Se])([Se]2)C3=CC=CC=C3
Properties
Chemical formula	C12H10P2Se4
Molar mass	532.04 g·mol−1
Appearance	red powder
Melting point	192 to 204 °C (378 to 399 °F; 465 to 477 K)
Solubility in water	soluble in toluene at elevated temperatures
Vapor pressure	{{{value}}}
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Woollins' reagent is an organic compound containing phosphorus and selenium. Analogous to Lawesson's reagent, it is used mainly as a selenation reagent. It is named after Professor John Derek Woollins, who is currently the Vice Principal of Research at the University of St Andrews.

Preparation

Woollins' reagent is commercially available. 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). An alternative synthesis is the reaction of the pentamer (PPh)₅ with elemental selenium.

Applications

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