Photolytic decarbonylation of o-benzoquinones

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-...

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Bibliographic Details
Published in:Tetrahedron 2008-10, Vol.64 (41), p.9784-9788
Main Authors: Shurygina, M.P., Kurskii, Yu.A., Druzhkov, N.O., Chesnokov, S.A., Abakumova, L.G., Fukin, G.K., Abakumov, G.A.
Format: Article
Language:English
Subjects:
Cyclopentadienone
Decarbonylation
o-Benzoquinone
Photolysis
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Summary: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 (bicyclo[1.3.0]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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.07.008