6 of 6
NISHIDA ET AL.
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4 | CONCLUSIONS
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The use of 3Ac as a mild amine acetylating agent was
examined, and the reactions proved to be sensitive to ste-
ric and polar effects of the attacking nucleophile.
Aminolysis of 3Ac is somewhat faster than the corre-
sponding reactions with 2‐naphthylacetate, which is most
probably due to the intramolecular assistance of the car-
boxylate group. This hypothesis is supported by DFT cal-
culations which indicate that the o‐carboxy group plays
a pivotal role, guiding the attacking amine and accelerat-
ing the reaction. The reaction of 3Ac can be used for the
selective acetylation of primary amino groups in diamines
as well in amino alcohols, and we are in the process of
examining the wider scope of this intramolecularly cata-
lyzed reaction.
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