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

ABSTRACT: 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.

SUBMITTER: Chakiri AB

PROVIDER: S-EPMC5579107 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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

Chakiri Abdel B AB Hodge Philip P

Royal Society open science 20170823 8

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. ...[more]

PMID: 28878991

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