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Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes.

ABSTRACT: Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.

SUBMITTER: Luan Y

PROVIDER: S-EPMC4655818 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes.

Luan Yi Y Sun Huan H Schaus Scott E SE

Organic letters 20111118 24

Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway. ...[more]

PMID: 22098535

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