Structure and reactions of photothebainehydroquinone |
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| Authors: | Z.J. Barneis R.J. Warnet D.M.S. Wheeler |
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| Affiliation: | Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68508 USA; Chemical Laboratory, University of Sussex, Brighton, England |
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| Abstract: | The structure of photothebainehydroquinone, which was obtained by unsensitized irradiation with UV light of thebainequinone (1) or thebainehydroquinone (2) has been shown by X-ray crystallography to be 3a, which arises from 2 through a di-π-methane to vinylcyclopropane rearrangement. Treatment of 3a with acid gave 5a, 6a, 5b and probably 6b. Studies using DCl showed that the opening of the cyclopropane in 3a to give 5a, 5b, and 6a involved ‘end-on’ approach of the D+. The mechanisms of the reactions are discussed. |
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