1097663-55-2Relevant academic research and scientific papers
A natural light induced regioselective 6π-electrocyclisation-oxidative aromatisation reaction: Experimental and theoretical insights
Moulton, Benjamin E.,Dong, Hao,O'Brien, Ciara T.,Duckett, Simon B.,Lin, Zhenyang,Fairlamb, Ian J. S.
experimental part, p. 4523 - 4532 (2009/03/12)
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 6π-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.
