Woollins' reagent

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Structural formula
Structural formula of Woollins' reagent
General
Surname Woollins' reagent
other names

2,4-diphenyl-1,3,2,4-diselenadiphosphetane-2,4-diselenide

Molecular formula C 12 H 10 P 2 Se 4
Brief description

red crystals

External identifiers / databases
CAS number 122039-27-4
EC number 627-200-6
ECHA InfoCard 100.155.582
PubChem 5066075
Wikidata Q415207
properties
Molar mass 532.00 g mol −1
Physical state

firmly

Melting point

192-204 ° C

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment

danger

H and P phrases H: 301-331-373-410
P: 261-273-301 + 310-311-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Woollins' reagent is a chemical, more precisely an organic compound containing phosphorus and selenium, and can be regarded as the selenium analogue of Lawesson's reagent .

Manufacturing

Woollins' reagent is synthesized in high purity and yield from the reaction of dichlorophenylphosphine with sodium selenide (produced by reacting elemental selenium with sodium in liquid ammonia ). Alternatively, it can also be produced by the reaction of the pentamer (PPh) 5 with elemental selenium.

use

Woollins' reagent has been found useful in the preparation of selenocarbonyl compounds from carbonyl compounds . The synthesis of selenoamides (selenium analogues of carboxamides and thionamides ) and selenoaldehydes (selenium analogues of aldehydes ) has been described. The reaction of Woollins' reagent with carboxylic acids , alkenes , alkynes and nitriles is also known.

See also

Lawesson's reagent

Individual evidence

  1. ↑ a b The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1731, ISBN 978-0-911910-00-1 .
  2. ↑ a b c Datasheet Woollins' Reagent from Sigma-Aldrich , accessed on May 25, 2017 ( PDF ).
  3. ↑ Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the indicated labeling it falls under the group entry selenium compounds with the exception of cadmium sulphoselenide and those specified elsewhere in this Annex in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Ian P. Gray, Pravat Bhattacharyya, Alexandra MZ Slawin, J. Derek Woollins: A New Synthesis of (PhPSe2) 2 (Woollins Reagent) and Its Use in the Synthesis of Novel P-Se Heterocycles. In: Chemistry - A European Journal. 11, 2005, pp. 6221-6227, doi : 10.1002 / chem.200500291 .
  5. ↑ MJ Pilkington, Alexandra MZ Slawin and J. Derek Woollins, Heteroatom Chemistry 1990 , 351.
  6. ↑ Pravat Bhattacharyya and J. Derek Woollins: Selenocarbonyl synthesis using Woollins reagent in Tetrahedron Letters 42 (2001) 5949-5951, doi : 10.1016 / S0040-4039 (01) 01113-3 .
  7. ↑ Pravat Bhattacharyya, Alexandra MZ Slawin and J. Derek Woollins: Heterocycle formation using [PhP (Se) (μ-Se)] 2 . The crystal structures of [PhP (Se) (μ-Se)] 2 , PhP (Se) Se 2 (C 7 H 10 ) and PhP (Se) (μ-Se) (μ-NPh) P (Se) Ph in J. Chem. Soc. Dalton Trans. 2001 , 300-303, doi : 10.1039 / B008071N .