Journal of Organic Chemistry p. 3869 - 3876 (1993)
Update date:2022-08-03
Topics:
Kruper, William J.
Rudolf, Philip R.
Langhoff, Charles A.
Reaction of equivalent amounts of free base polyazamacrocycles with an alkyl halide in a nonpolar, aprotic solvent affords the mono-N-alkylation product as its monohydrohalide salt in high yield with excellent selectivity.This unexpected selectivity has been explained in terms of the high affinity of the alkylated product for a single proton which attenuates the nucleophilicity of the remaining nitrogen atoms.Selectivity is dependent upon a number of factors including macrocycle ring size, solvent polarity, and the steric nature of the electrophile.The approach has been allowed for a short, convergent route to bifunctional lanthanide chelators which are useful in therapeutic applications.
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