title: 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.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Life Sciences and Engineering Building, Boston University, 24 Cummington Street, Boston, Massachusetts 02215, USA.
authors.forename: Yi
authors.initials: Y
authors.lastname: Luan
authors.forename: Huan
authors.initials: H
authors.lastname: Sun
authors.forename: Scott E
authors.initials: SE
authors.lastname: Schaus
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D045563:Indolequinones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D005290:Ferric Compounds; D006571:Heterocyclic Compounds; D045563:Indolequinones; C068040:quinone methide
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