学術雑誌論文 Contraction of π-Conjugated Rings upon Oxidation from Cyclooctatetraene to Benzene via the Tropylium Cation

Tamoto, Akira  ,  Aratani, Naoki  ,  Yamada, Hiroko

2017-10-25 , Wiley-VCH Verlag
ISSN:1521-3765
内容記述
We have serendipitously discovered a unique transformation of a cyclooctatetraene derivative 1 into a cycloheptatriene spirolactone 3 upon oxidation, which is the first such transformation reported in 60 years. Product 3 could be reversibly interconverted into the aromatic tropylium cation 3H+ by acid/base treatment, which was accompanied by drastic spectroscopic changes. The resultant cycloheptatriene could be further converted into benzene upon oxidation. We characterized all the key structures by X-ray studies. Eventually, the π-conjugated ring size shrinks from 8 to 7, then finally to 6 upon oxidation, in the direction of the stronger aromatization.
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http://dx.doi.org/10.1002/chem.201704008

http://library.naist.jp/dspace/xmlui/bitstream/10061/12186/1/revised_TextNA.pdf

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