Woollins' reagent

Woollins' Reagent
IUPAC name

2,4-Diphenyl-1,3,2,4-
diselenadiphosphetan-2,4-diselenide
Other names

Woollins' Reagent
Identifiers
CAS number 122039-27-4
Properties
Molecular formula C12H10P2Se4
Molar mass 532 g mol−1
Appearance red powder
Melting point

192–204 °C[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
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 head of chemistry 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 elementary 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/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. 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 and 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 and J. Derek Woollins (2009). "Formation and Reactivity of Phosphorus-Selenium Rings". Angew. Chemie., Int. Ed. 48 (8): 1368–1377. doi:10.1002/anie.200800572. PMID 19053094.