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Factors Influencing the Course of the Macrocyclization of α , ω ‐Diamines with Esters of α , ω ‐Dicarboxylic Acids
Author(s) -
Gryko Dorota,
Gryko Daniel T.,
SierzputowskaGracz Hanna,
Pia̧tek Piotr,
Jurczak Janusz
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490004
Subject(s) - chemistry , steric effects , intermolecular force , dilution , stereochemistry , diamine , organic chemistry , molecule , thermodynamics , physics
The efficient synthesis of eight new macrocyclic amides (lactams) via reaction of diesters with diamines under normal dilution conditions is described. The role of intermolecular H‐bond formation and steric hindrance is discussed based on 1 H‐ and 15 N‐NMR studies of appropriate model compounds. Principles for the optimal choice of esters that can be efficiently transformed into diamides have been developed.