Photochemistry of 3-substituted bicyclo[3.1.0]hex-3-en-2-ones. Regioselective synthesis of ortho-substituted phenols by Pauson-Khand reaction |
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Authors: | Marchueta I Olivella S Solà L Moyano A Pericàs M A Riera A |
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Affiliation: | Departament de Química Orgànica, Martí i Franquès, 1-11, Barcelona E-08028, Spain. |
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Abstract: | [reaction: see text] 3-Substituted bicyclo[3.1.0]hex-3-en-2-ones 3, easily obtained by Pauson-Khand reaction between terminal alkynes and cyclopropene, have been quantitatively converted into ortho-substituted phenols 4 by irradiation with UV light (350 nm). The kinetics and mechanism of this photochemical process have been studied by means of FT-IR and semiempirical (AM1 3x3 CI) calculations. |
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