Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups | Zendy

Abdel B. Chakiri | Zendy; Philip Hodge | Zendy

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Synthesis of isopropyl-substituted anthraquinones via Friedel–Crafts acylations: migration of isopropyl groups

Author(s) -

Abdel B. Chakiri,

Philip Hodge

Publication year - 2017

Publication title -

royal society open science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.84

H-Index - 51

ISSN - 2054-5703

DOI - 10.1098/rsos.170451

Subject(s) - isopropyl , friedel–crafts reaction , phthalic anhydride , anthraquinones , anthraquinone , chemistry , sulfuric acid , ring (chemistry) , organic chemistry , medicinal chemistry , catalysis , botany , biology

Friedel–Crafts reactions of isopropyl-substituted benzenes with phthalic anhydride in the presence of aluminium trichloride, followed by cyclization of the products with strong sulfuric acid give, as expected, anthraquinones. The syntheses, however, often afford more than one anthraquinone. In some cases the isopropyl groups migrate cleanly to other ring positions; in other cases they are lost.

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