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A natural light induced regioselective 6 pi-electrocyclisation-oxidative aromatisation reaction: experimental and theoretical insights

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JournalOrganic and Biomolecular Chemistry
DatePublished - 2008
Issue number24
Volume6
Number of pages10
Pages (from-to)4523-4532
Original languageEnglish

Abstract

Stoichiometric intermolecular Pauson-Khand reactions of 4-(phenylethynyl)-6-methyl-2-pyrones with norbornene and dicobalt(0) octacarbonyl provide cyclopentenone products that undergo a facile 6p-electrocyclisation-oxidative aromatisation transformation in the presence of natural light and oxygen, affording functionalised benzo[h]indeno[1,2-f]isochromene type products. The results are rationalised by theoretical studies, which confirm that the electrocyclisation process is favoured at C3 in the 2-pyrone ring system. The identity and precise arrangement of the 'trienyl' substituents control whether the electrocyclisation occurs in natural light.

    Research areas

  • IRREVERSIBLE PHOTOCHROMIC SYSTEMS, PAUSON-KHAND REACTION, EXPLORATORY ORGANIC-PHOTOCHEMISTRY, REVERSIBLE PHOTOCYCLIZATION, DIARYLETHENE DERIVATIVES, SELECTIVE SYNTHESIS, COUPLING REACTIONS, DICTYODENDRIN-B, SEX-PHEROMONE, 3,5-DIBROMO-2-PYRONE

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