Highly diastereoselective Diels-Alder cycloadditions of 9R-(1-methoxyethyl)anthracene with p-benzoquinone.
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.
Adams
Harry
H
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, UK.
Jones
Simon
S
Ojea-Jimenez
Isaac
I
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
D000873:Anthracenes; D016227:Benzoquinones; C004532:quinone