Woollins’ Reagent

Introduction

Woollins’ Reagent {WR, 2,4-diphenyl-1,3-diselenadi-phosphetane-2,4-diselenide, [PhP(Se)(µ-Se)]₂} is a selenium analogue of the well-known Lawesson’s reagent, [4-MeOC₆H₄P(S)(µ-S)]₂. Compared to other selenium reagents, the deep-red crystals of WR have less unpleasant chemical properties, are easy to prepare, and safely handled in air. [¹] WR is used in the synthesis of selenium-­containing organic compounds and P-Se heterocycles. [²]

Woollins and co-workers initially prepared WR from the pentamer (PhP)₅, [³] which is an air-sensitive compound with a lingering stench. For this reason, they have developed a new method preparing WR producing material of high purity in high yield. [4] This compound is now commercially available.

Figure 1

References

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• 2 Hua G. Woollins JD. Angew. Chem. Int. Ed.  2009,  48:  1368 
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• 6 Bhattacharyya P. Woollins JD. Tetrahedron Lett.  2001,  42:  5949 
• 7 Bethke J. Karaghiosoff K. Wessjohann LA. Tetrahedron Lett.  2003,  44:  6911 
• 8 Hua G. Li Y. Slawin AMZ. Woollins JD. Org. Lett.  2006,  8:  5251 
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• 13 Hua G. Li Y. Slawin AMZ. Woollins JD. Chem. Commun.  2007,  1465 
• 14 Hua G. Zhang Q. Li Y. Slawin AMZ. Woollins JD. Dalton Trans.  2008,  5563