A Straightforward Access to Stable β-Functionalized Alkyl Selenols

Treatment of epoxides with bis(trimethylsilyl)-selenide under strictly controlled conditions allows to isolate b-hydroxy selenols which evidence an unexpected stability, taking into account their known propensity to afford diselenides. Also thiiranes and aziridines lead to functionalized selenols bearing a thiol and a N-Ts- or N-Boc-protected amino moiety on b-position. These selenols were stable enough to react with different electrophiles. Ab-initio DF calculations on two suitable model systems, n-propyl selenol and bhydroxy derivative, allow to ascribe the observed low tendency to oxidation to noncovalent interactions between the selenol moiety and theOH group.