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A Scalable Process for the Synthesis of 1,2-Dialkyldiselanes and 1‑Alkaneselenols
journal contribution
posted on 2019-10-29, 15:06 authored by John P. Cooksey, Philip J. Kocieński, A. John BlackerA four-step
telescoped process for the synthesis of 1-alkaneselenols
entails (1) the rapid formation of potassium selenocyanate from potassium
cyanide and selenium in methanol, (2) the nucleophilic substitution
of bromoalkanes or alkyl tosylates with potassium selenocyanate, (3)
the mild base-catalyzed conversion of the resultant 1-alkaneselenocyanates
to 1,2-dialkyldiselanes (the Krief reaction), and (4) the reduction
of the resultant 1,2-dialkyldiselanes with hypophosphorous acid to
give the desired 1-alkaneselenols. The process has been used to produce
1-octaneselenol on a 10.4 mol scale. Nine examples of the process
are described.