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DOI: 10.1055/s-2005-864814
Condition-Driven Selective Syntheses of Dialkyl Diselenides Involving Elemental Selenium and Sodium Borohydride
Publication History
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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Synthesized by protonation (formic acid, 2.5-4 equiv) of selenide dianion equivalent [from elemental selenium, NaBH4 and EtOH (1:2:6) in DMF]. [13a]
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in fact, we found in a control experiment that 6 molar equiv of dihydrogen escape from the medium (experimentally 97% of this amount) on reaction of selenium, NaBH4 and EtOH (1:2:6 mol equiv).
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Another 0.81 molar equiv of dihydrogen is evolved if aq EtOH (4 molar equiv each), is added before that of the second crop of elemental selenium.
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References
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).