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Synlett 2005(11): 1755-1757  
DOI: 10.1055/s-2005-871550
LETTER
© Georg Thieme Verlag Stuttgart · New York

On the Role of Triethyl Borate in the Reduction of Elemental Selenium, Diselenide Dianions, Sodium Decyl Diselenolate, and Didecyl Diselenide with Sodium Borohydride

Alain Krief*a, Michel Derocka,b
a Laboratoire de Chimie Organique de Synthèse, Facultés Universitaires N.-D. de la Paix, 61 Rue de Bruxelles, Namur 5000, Belgium
Fax: +32(81)724536; e-Mail: alain.krief@fundp.ac.be;
b Fonds pour la Formation à la Recherche dans l’Industrie et l’Agriculture, 5 Rue d’Egmont, Bruxelles 1000, Belgium
Further Information

Publication History

Received 27 March 2005
Publication Date:
28 June 2005 (online)

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Abstract

Addition of triethyl borate to disodium diselenide or to sodium decyl diselenolate allows their reduction with sodium borohydride which otherwise does not take place.

Key words

selenium - reduction - sodium borohydride

    References

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    Disodium diselenide has been prepared, as already described as a brownish solution, from elemental selenium and either NaH in DMF (1 equiv each, 70 °C, 2 h) [3a] or sodium in liquid NH3 (1 equiv each) [3b] and replacement of the NH3 by DMF.
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6

During the course of this work we observed that triethyl borate is produced besides didecyl selenide on sequential reaction of elemental selenium, sodium borohydride, ethanol and decyl bromide (Equation [1] , entry a). It has been distilled, in quantitative yield, from the crude mixture and compared to an authentic sample purchased from the Sigma Aldrich Company. It was nevertheless impossible to distill it out of the medium before addition of decyl bromide although it was easy to remove the solvent (heating up to 120 °C) from the reaction mixture.