Synthesis of Bromo‐Substituted 4‐Hydroxy[2.2]paracyclophanes and [2.2]Paracyclophane‐4,7‐quinones as Versatile Chiral Building Blocks | Zendy

Atman Vorontsova Natalia V. | Zendy; Zhuravsky Roman P. | Zendy; Antonov Dmitrii Yu. | Zendy; Sergeeva Elena V. | Zendy; Godovikov Ivan A. | Zendy; Starikova Zoya A. | Zendy; Vologzhanina Anna V. | Zendy

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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.

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