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Woollins' reagent

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Organic compound
Woollins' Reagent
Skeletal formula of Woollins' reagent
3D model of the Woollins' reagent molecule
Names
Preferred IUPAC name 2,4-Diphenyl-1,3,2λ,4λ-diselenadiphosphetane-2,4-diselone
Other names Woollins' Reagent
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.582 Edit this at Wikidata
EC Number
  • 627-200-6
PubChem CID
UNII
CompTox Dashboard (EPA)
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/h1-10HKey: 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/h1-10HKey: GKYFQRQKPYPLGJ-UHFFFAOYAX
SMILES
  • c1ccccc1P2(=)P(=)(2)c3ccccc3
Properties
Chemical formula C12H10P2Se4
Molar mass 532.044 g·mol
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
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H331, H373, H410
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 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). An alternative synthesis is the reaction of the pentamer (PPh)5 (pentaphenylcyclopentaphosphine) 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.

References

  1. The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14. Auflage, 2006, S. 1731, ISBN 978-0-911910-00-1
  2. Ian P. Gray, Pravat Bhattacharyya, Alexandra 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.
  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.
  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.
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