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Single‐Step, Regioselective Synthesis of Diazadioxacalix[4]arenes and Diazadioxa[1 4 ]cyclophanes Bearing an Alternating N/O‐Bridge Pattern
Author(s) -
Bizier Nicholas P.,
Vernamonti Jack P.,
Katz Jeffrey L.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200137
Subject(s) - chemistry , regioselectivity , cyclophane , bridge (graph theory) , condensation , stereochemistry , selectivity , chemical synthesis , crystallography , organic chemistry , crystal structure , catalysis , physics , thermodynamics , biochemistry , in vitro , medicine
Described is a single‐step synthesis of diazadioxacalix[4]arenes and diazadioxa[1 4 ]cyclophanes bearing an alternating N/O‐bridge substitution pattern. The macrocycles are formed regioselectively by condensation of 3‐ or 4‐aminophenols with 1,5‐difluoro‐2,4‐dinitrobenzene. Conformational properties of the macrocyclic products are discussed, as well as mechanistic details of the synthesis leading to the observed bridge‐pattern selectivity.