Premium
Synthesis of Bromo‐Substituted 4‐Hydroxy[2.2]paracyclophanes and [2.2]Paracyclophane‐4,7‐quinones as Versatile Chiral Building Blocks
Author(s) -
Atman Vorontsova Natalia V.,
Zhuravsky Roman P.,
Antonov Dmitrii Yu.,
Sergeeva Elena V.,
Godovikov Ivan A.,
Starikova Zoya A.,
Vologzhanina Anna V.
Publication year - 2015
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.201403316
Subject(s) - chemistry , regioselectivity , bromine , phenol , phenols , cyclophane , halogenation , combinatorial chemistry , stereochemistry , transformation (genetics) , organic chemistry , molecule , catalysis , biochemistry , gene
Approaches to a number of bromo‐substituted derivatives of 4‐hydroxy[2.2]paracyclophane, including the regioselective mono‐ and dibromination of this phenol, were investigated. The applicability of the regioisomeric monobromo‐substituted phenols for the synthesis of substituted [2.2]paracyclophane‐4,7‐quinones through a one‐pot diazonium coupling/reduction/oxidation sequence was demonstrated. The compounds obtained possess various substitution patterns and could be used for the synthesis of a wide range of [2.2]paracyclophane derivatives by transformation of the bromine, hydroxy, and quinoid fragments.