Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 64, Pages 16388-16392Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704008
Keywords
aromaticity; cyclooctatetraene; oxidation; rearrangement; pi-conjugation
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Funding
- CREST JST [JPMJCR15F1]
- JSPS KAKENHI [JP17H03042, JP16H02286, JP26105004, JP15H00876]
- MEXT
- Grants-in-Aid for Scientific Research [16H02286] Funding Source: KAKEN
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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 pi-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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