Synlett 2012; 23(12): 1847-1848
DOI: 10.1055/s-0031-1290430
spotlight
© Georg Thieme Verlag Stuttgart · New York

Sodium Selenide

Rui-Yun Guo
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, P. R. of China, Email: guoruixiaonihao@sohu.com
› Author Affiliations
Further Information

Publication History

Publication Date:
05 July 2012 (online)

Introduction

Sodium selenide is an odourless white crystalline solid, which is soluble in water. Sodium selenide is very useful in the preparation of a wide variety of selenium-containing heterocycles.[ 1 ] It can be used for the synthesis of substituted selenophenes, [2] [3] nitroxide annulated 3-amino-2-(ethoxycarbonyl)selenophene,[ 4 ] bis(2,4,6-trimethylphenyl)selenide,[ 5 ] phosphinodiselenoic acid salt,[ 6 ] unsaturated selenacrown ethers,[ 7 ] diselenobenzoquinone complexes,[ 8 ] and 1,4-dichalcogenanes.[ 9 ] In addition, it has been employed in the ring opening of epoxides[ 10 ] and γ-butyrolactones.[ 11 ]

Sodium selenide is commercially available and can be prepared by reduction of elemental selenium with sodium in liquid ammonia (Scheme [1]).[ 12 ]

Zoom Image
Scheme 1
 
  • References

  • 1 Sommen GL, Thomae D. Curr. Org. Synth. 2010; 7: 44
  • 2 Rhoden CR. B, Zeni G. Org. Biomol. Chem. 2011; 9: 1301
  • 3 Thomae D, Kirsch G, Seck P. Synthesis 2008; 1600
  • 4 Kálai T, Bagi N, Jekő J, Berente Z, Hideg K. Synthesis 2010; 1702
  • 5 Ghavale N, Phadnis PP, Wadawale A, Jain VK. Indian J. Chem. 2011; 50A: 22
  • 6 Kimura T, Murai T. J. Org. Chem. 2005; 70: 952
  • 7 Shimizu T, Kawaguchi M, Tsuchiya T, Hirabayashi K, Kamigata N. J. Org. Chem. 2005; 70: 5036
  • 8 Amouri H. Synlett 2011; 1357
  • 9 Martynov AV, Larina LI, Amosova SV. Tetrahedron Lett. 2012; 53: 1218
  • 10 Scianowski J, Rafinski Z, Wojtczak A, Burczynski K. Tetrahedron: Asymmetry 2009; 20: 2871
  • 11 Krief A, Derock M. Synlett 2005; 1012
  • 12 Woollins JD. Synlett 2012; 1154
  • 13 Potapov VA, Elokhina VN, Larina LI, Yaroshenko TI, Tatarinova AA, Amosova SV. J. Organomet. Chem. 2009; 694: 3679
  • 14 Li DW, Xu XX, Liu Q, Dong S. Synthesis 2008; 1895
  • 15 Amosova SV, Martynov AV. Russ. J. Org. Chem. 2011; 47: 1772
  • 16 Potapov VA, Amosova SV, Doron’kina IV, Korsun OV. J. Organomet. Chem. 2003; 674: 104
  • 17 Sommen G, Comel A, Kirsch G. Synlett 2003; 855
  • 18 Thomae D, Dominguez JC. R, Kirsch G, Seck P. Tetrahedron 2008; 64: 3232
  • 19 Thomae D, Perspicace E, Henryon D, Xu ZJ, Schneider S, Hesse S, Kirsch G, Seck P. Tetrahedron 2009; 65: 10453
  • 20 Sommen GL. Mini-Rev. Org. Chem. 2005; 2: 375