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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 2
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Original Articles

Convenient Preparation of Dialkyl Diselenides: A Large Scale Synthesis of bis-(2-Hydroxyethyl) Diselenide

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Pages 195-199 | Received 31 Jul 1992, Published online: 23 Sep 2006

References

  • Guelph-Waterloo Centre for Graduate Work in Chemistry , Waterloo ON, , Canada : Univ. of Waterloo . Waterloo Campus, Dept. of Chemistry, N2L 3G1.Present address
  • Present address: MKM Laboratories, Ltd., R. R. #3, Rockwood, ON., Canada N0B 2K0
  • Clive , D. L. J. 1978 . Tetrahedron , 34 : 1049 For reviews see:
  • Krief , A. 1980 . Tetrahedron , 36 : 2531
  • Kang , S. I. and Spears , C. P. 1987 . J. Med. Chem. , 30 : 597
  • Spallholz , J. E. , Martin , J. L. and Ganther , H. E. , eds. 1981 . “Selenium in Biology and Medicine” , Westport, CT : AVI Publishing Co. . Compound 2 (i.e. R ═ H and X ═ OH) has been studied in connection with the known, although not well understood, protective effects of selenium against methylmercury (II) poisoning:These compounds have other interesting properties too (for a review of the biological activity of Se compounds see
  • Arnold , A. P. , Tan , K. S. and Rabenstein , D. L . 1986 . Inorg. Chem. , 25 : 2433
  • Tan , K. S. , Arnold , A. P. and Rabenstein , D. L. 1988 . Can. J. Chem. , 66 : 54 and the mode of action of seleno enzymes
  • Kang , S. I. and Spears , C. P. 1988 . Synthesis , : 133
  • Schwarz , K. and Fredga , A. 1974 . Bioinorg. Chem. , 3 : 153 Compound 3 also has interesting biological properties. Its high activity in the prevention of dietary liver necrosis has been reported
  • Yarovenko , N. N. , Raksha , M. A. and Shemanina , V. N. 1960 . Zh. Obshch. Khim. , 30 : 4069
  • Lindgren , B. 1977 . Acta Chem. Scand , B31 : 1
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  • Syper , L. and Mlochowski , J. 1984 . Synthesis , : 439
  • Korchevin , N. A. , Podkuiko , P. A. , Stankevich , V. K. , Deryagina , E. N. and Voronkov , M. G. 1989 . Zh. Obshch. Khim. , 59 : 1788
  • This is important because, as noted in reference 8, compound 3 partially decomposes upon distillation (bp 166–168°C/0.25 torr; lit.8 169–179°C/1.6–4.0 mmHg). While other authors using this method do not mention this phenomenon (see for example references 4a and 4b), we have consistently observed precipitation of elemental Se and decomposition upon heating this material
  • McPhee , D. J. and Jakiwczyk , Olga M. unpublished results.
  • McPhee , D. J. unpublished results. The method used is described in reference 8

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