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Chiral Anthranyl Trifluoromethyl Alcohols: Structures, Oxidative Dearomatization and Chiroptical Properties

dc.rights.licenseopenen_US
dc.contributor.authorSONET, Dorian
dc.contributor.authorCAYLA, Matteo
dc.contributor.authorMÉREAU, Raphael
dc.contributor.authorMORVAN, Estelle
dc.contributor.authorLACOUDRE, Aline
dc.contributor.authorVANTHUYNE, Nicolas
dc.contributor.authorALBALAT, Muriel
dc.contributor.authorBASSANI, Dario M.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorSCALABRE, Antoine
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorPOUGET, Emilie
dc.contributor.authorBIBAL, Brigitte
dc.date.accessioned2023-03-28T08:11:43Z
dc.date.available2023-03-28T08:11:43Z
dc.date.issued2022-12-27
dc.identifier.issn0947-6539en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/172636
dc.description.abstractEnAbstract Chiral trifluoromethyl alcohol groups were introduced at the hindered ortho positions of 9,10-diphenylanthracenes to investigate their effects on the physical properties and reactivity towards oxidative dearomatization. In such compact structures, the position in different quadrants and the preferred orientation of the ?CH(OH)CF3 groups were determined by the relative and absolute configurations of each stereoisomer, respectively. As a consequence, the stereochemistry governs the organization of the H-bonded molecules in single crystals (homochiral dimers vs ribbon), whereas in chlorinated solvents, they all behave as discrete compounds. Concerning their reactivity, the stereospecific dearomative oxidation of these molecules leads to 9,10-bis-spiro-isobenzofuran-anthracenes, when using organic single-electron transfer oxidants. The chiroptical properties of the alcohols and the corresponding dearomatized products were compared and showed an important modulation of the intensity.
dc.language.isoENen_US
dc.title.enChiral Anthranyl Trifluoromethyl Alcohols: Structures, Oxidative Dearomatization and Chiroptical Properties
dc.typeArticle de revueen_US
dc.identifier.doi10.1002/chem.202202695en_US
dc.subject.halChimie/Matériauxen_US
bordeaux.journalChemistry – A European Journalen_US
bordeaux.volume28en_US
bordeaux.hal.laboratoriesCBMN : Chimie & de Biologie des Membranes & des Nano-objets - UMR 5248en_US
bordeaux.issue72en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionCNRSen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.exportfalse
dc.rights.ccPas de Licence CCen_US
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20%E2%80%93%20A%20European%20Journal&rft.date=2022-12-27&rft.volume=28&rft.issue=72&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=SONET,%20Dorian&CAYLA,%20Matteo&M%C3%89REAU,%20Raphael&MORVAN,%20Estelle&LACOUDRE,%20Aline&rft.genre=article


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