The conventional Wenker synthesis of aziridines from vicinal
amino alcohols has been modified by employing mild reaction conditions.
Amino alcohols were converted into their hydrogen sulfates with
chlorosulfonic acid. The sulfates were cyclized with sodium hydroxide,
and even with non-nucleophilic sodium carbonate. The current, improved
method extends the scope of the typical Wenker synthesis and is
applicable to unstable amino alcohols in hot sulfuric acid and to
unstable sulfates which favor elimination and hydroxide displacement
in the presence of strong base.
amino alcohols - aziridines - hydrogen sulfates - Wenker synthesis
