Woollins' reagent

Woollins' Reagent
Names
	IUPAC name 2,4-Diphenyl-1,3,2,4-diselenadiphosphetan-2,4-diselenide
	Other names Woollins' Reagent
Identifiers
CAS Number	122039-27-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	4242993 ;
ECHA InfoCard	100.155.582
PubChem CID	5066075;
UNII	75551CT912 ;
CompTox Dashboard (EPA)	DTXSID60407970 ;
	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 c1ccccc1P2(=[Se])[Se]P(=[Se])([Se]2)c3ccccc3;
Properties
Chemical formula	C12H10P2Se4
Molar mass	532.044 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R-phrases (outdated)	R23/25 R33 R50/53
S-phrases (outdated)	(S1/2) S20/21 S28 S45 S60 S61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.

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

Applications

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.[5]

References

The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 1731, ISBN 978-0-911910-00-1.
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.CS1 maint: multiple names: authors list (link)
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): 351–355. doi:10.1002/hc.520010502.
Pravat Bhattacharyya & J. Derek Woollins (2001). "Selenocarbonyl synthesis using Woollins reagent". Tetrahedron Lett. 42 (34): 5949. doi:10.1016/S0040-4039(01)01113-3. hdl:10023/1776.
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.

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[MerckIndex-1] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 1731, ISBN 978-0-911910-00-1.

[gray-2] 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.CS1 maint: multiple names: authors list (link)

[pilkington-3] 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): 351–355. doi:10.1002/hc.520010502.

[Bhattacharyya-4] Pravat Bhattacharyya & J. Derek Woollins (2001). "Selenocarbonyl synthesis using Woollins reagent". Tetrahedron Lett. 42 (34): 5949. doi:10.1016/S0040-4039(01)01113-3. hdl:10023/1776.

[Hua-5] 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.