Woollins' reagent

Woollins' Reagent

Names
IUPAC names 2,4-Diphenyl-1,3,2,4- diselenadiphosphetan-2,4-diselenide
Other names Woollins' Reagent
Identifiers
CAS Number	122039-27-4
3D model (Jmol)	Interactive image
ChemSpider	4242993
ECHA InfoCard	100.155.582
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) [1]
Solubility in water	soluble in toluene at elevated temperatures
Hazards
R-phrases	R23/25 R33 R50/53
S-phrases	(S1/2) S20/21 S28 S45 S60 S61
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.^[2]

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).^[3] An alternative synthesis is the reaction of the pentamer (PPh)₅ with elemental selenium.^[4]

Applications

The main use of Woollins' reagent is the selenation of carbonyl compounds.^[5] 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.^[6]

References

1. The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 1731, ISBN 978-0-911910-00-1.
2. http://chemistry.st-andrews.ac.uk/staff/jdw/group/home.html
3. Ian P. Gray, Pravat Bhattacharyya, Alexandra M. Z. Slawin and J. Derek Woollins (2005). "A New Synthesis of (PhPSe2)2 (Woollins Reagent) and Its Use in the Synthesis of Novel P-Se Heterocycles". Chem. Eur. J. 11 (21): 6221–7. doi:10.1002/chem.200500291. PMID 16075451.
4. M. J. Pilkington, Alexandra M. Z. Slawin and J. Derek Woollins (1990). "The preparation and characterization of binary phosphorus-selenium rings". Heteroatom Chemistry. 1 (5): 351. doi:10.1002/hc.520010502.
5. Pravat Bhattacharyya & J. Derek Woollins (2001). "Selenocarbonyl synthesis using Woollins reagent". Tet. Lett. 42 (34): 5949. doi:10.1016/S0040-4039(01)01113-3.
6. Guoxiong Hua & J. Derek Woollins (2009). "Formation and Reactivity of Phosphorus-Selenium Rings". Angew. Chem. Int. Ed. 48 (8): 1368–1377. doi:10.1002/anie.200800572. PMID 19053094.