Alkylation of some diamines containing both tertiary and primary amino
groups is described; it proceeds exclusively with less nucleophilic t
ertiary amino group when an appropriate lanthanide chelate is added to
the reaction mixture. Under similar conditions the alkylation of 3-(t
etrahydro-2-thienyl)-pyridine affects both of its nucleophilic centers
. Plausible explanations of this fact is discussed. The effect of the
presence of different lanthanide complexes upon difunctional compound
alkylation has been investigated.