Photolytic decarbonylation of o-benzoquinones |
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Authors: | MP Shurygina YuA Kurskii NO Druzhkov SA Chesnokov LG Abakumova GK Fukin GA Abakumov |
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Institution: | G.A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 Tropinina Street, 603950 Nizhny Novgorod, Russian Federation |
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Abstract: | It was established that photodecarbonylation of o-benzoquinones occurs by irradiation not only by UV-light, but visible light (λ>520 nm) too. Study of the series of 4,5-di-substituted 3,6-di-tert-butyl-o-benzoquinones detected that the only product of photoreaction is the corresponding 3,4-di-substituted 2,5-di-tert-butyl-cyclopentadienone, which is formed in a yield close to quantitative. NMR monitoring of reaction of photodecarbonylation of o-benzoquinones detected that this is a two-stage process. In the first stage the photoexcited molecule of quinone rearranges into bicyclo compound (bicyclo1.3.0]hexa-3-en-2,6-dione) containing five- and three- membered cycles, which spontaneously decomposes during the following dark stage into cyclopentadienone and a molecule of CO. |
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Keywords: | Photolysis Decarbonylation o-Benzoquinone Cyclopentadienone |
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