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Synlett 2005(6): 1012-1014  
DOI: 10.1055/s-2005-864814
LETTER
© Georg Thieme Verlag Stuttgart · New York

Condition-Driven Selective Syntheses of Dialkyl Diselenides Involving Elemental Selenium and 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
b Fonds pour la Formation à la Recherche dans l’Industrie et l’Agriculture, 5 Rue d’Egmont, Bruxelles 1000, Belgium
Fax: +32(81)724536; e-Mail: alain.krief@fundp.ac.be;
Further Information

Publication History

Received 4 January 2005
Publication Date:
23 March 2005 (online)

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Abstract

Dialkyl diselenides have been prepared from alkyl ­halides, sodium borohydride and elemental selenium using two ­different methods. One of them involves the intermediate formation of diselenide dianion equivalent (-SeSe-).

Key words

elemental selenium - sodium borohydride - alkylation - alkyl halides - benzyl halides - dimetal diselenide

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14

Typically mixing elemental selenium, NaBH4 and EtOH (1:1:3 molar equiv each) leads to the evolvement of dihydrogen (2.58 molar equiv, 86% of the expected amount), sequential addition of DMF and decyl bromide produces an additional formation of hydrogen (0.42 molar equiv, 14% of the expected amount).