Woollins' Reagent
Skeletal formula of Woollins' reagent
3D model of the Woollins' reagent molecule
Names
Preferred IUPAC name
2,4-Diphenyl-1,3,2λ5,4λ5-diselenadiphosphetane-2,4-diselone
Other names
Woollins' Reagent
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.582
EC Number
  • 627-200-6
UNII
  • 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 ☒N
    Key: GKYFQRQKPYPLGJ-UHFFFAOYSA-N ☒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
  • c1ccccc1P2(=[Se])[Se]P(=[Se])([Se]2)c3ccccc3
Properties
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]
soluble in toluene at elevated temperatures
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H331, H373, H410
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
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 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 (pentaphenylcyclopentaphosphine) 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

  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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