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RESEARCH PRODUCT
1,4-Benzoquinones with Styryl Substituents
Herbert MeierIsabella BrehmSabine Hinneschiedtsubject
Nucleophilic additionStereochemistryChemistryDimerOrganic ChemistryTautomerMedicinal chemistryCycloadditionchemistry.chemical_compoundNucleophileIntramolecular forceMoietyDehydrogenationPhysical and Theoretical Chemistrydescription
2-Styryl-1,4-benzoquinone (1) and compounds 2 and 3 containing 1 as a substructure all proved to be highly reactive towards thermal or photochemical [4π + 2π] cyclodimerization reactions. Chemo-, regio- and stereoselective processes lead to dimers (compounds 1−10), which can undergo secondary reactions consisting of the addition of nucleophiles combined with a twofold keto-enol tautomerism (10 ⇄ 12). An alternative process is dehydrogenation/oxidation followed by an intramolecular [4π + 2π] cycloaddition (10 ⇄ 11). The same selective [4π + 2π] cyclodimerization can be observed in solution upon irradiation (e.g., 1a ⇄ 10a), in contrast to irradiation in the crystalline state which yields a [2π + 2π] dimer (e.g., 1a ⇄ 13). If more than one styrylbenzoquinone moiety is present in the same molecule the oligomers 2a (n = 1−3) and 3a (n = 1−4) are obtained. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-09-01 | European Journal of Organic Chemistry |