title: Highly diastereoselective Diels-Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone.
abstract: Diels-Alder cycloadditions of p-benzoquinone with 9R-(1-methoxyethyl)anthracene provides a 60:40 ratio of cycloadducts when heated at reflux in xylene. Mechanistic studies to explore the origins of this selectivity have shown that at lower temperatures the kinetic product predominates, giving a 96:4 ratio of cycloadducts.
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, UK.
authors.forename: Harry
authors.initials: H
authors.lastname: Adams
authors.forename: Simon
authors.initials: S
authors.lastname: Jones
authors.forename: Isaac
authors.initials: I
authors.lastname: Ojea-Jimenez
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry*; D016227:Benzoquinones / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000873:Anthracenes; D016227:Benzoquinones; C004532:quinone