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Contraction of π-Conjugated Rings upon Oxidation from Cyclooctatetraene to Benzene via the Tropylium Cation

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dc.contributor.author Tamoto, Akira en
dc.contributor.author Aratani, Naoki en
dc.contributor.author Yamada, Hiroko en
dc.date.accessioned 2017-12-14T05:13:19Z en
dc.date.available 2017-12-14T05:13:19Z en
dc.date.issued 2017-10-25 en
dc.identifier.issn 1521-3765 en
dc.identifier.uri http://hdl.handle.net/10061/12186 en
dc.description.abstract 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. ja
dc.language.iso en en
dc.publisher Wiley-VCH Verlag en
dc.rights Copyright c 2017 WILEY-VCH Verlag en
dc.rights This is the peer reviewed version of the following article: Chem. Eur. J. 25 Oct. 2017;23(64): 16388-16392, which has been published in final form at 10.1002/chem.201704008. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. en
dc.rights 出版社許諾条件により本文は2018/10/25以降に公表する。 ja
dc.subject aromaticity en
dc.subject cyclooctatetraene en
dc.subject oxidation en
dc.subject rearrangement en
dc.subject π-conjugation ja
dc.title Contraction of π-Conjugated Rings upon Oxidation from Cyclooctatetraene to Benzene via the Tropylium Cation ja
dc.type.nii Journal Article en
dc.contributor.transcription アラタニ, ナオキ ja
dc.contributor.transcription ヤマダ, ヒロコ ja
dc.contributor.alternative 荒谷, 直樹 ja
dc.contributor.alternative 山田, 容子 ja
dc.textversion author en
dc.identifier.ncid AA11617391 en
dc.identifier.jtitle Chemistry - A European Journal en
dc.identifier.volume 23 en
dc.identifier.issue 64 en
dc.identifier.spage 16388 en
dc.identifier.epage 16392 en
dc.relation.doi 10.1002/chem.201704008 en
dc.identifier.NAIST-ID 73299042 en
dc.identifier.NAIST-ID 73293565 en
dc.relation.pmid 28913880 en


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