Chiral Anthranyl Trifluoromethyl Alcohols: Structures, Oxidative Dearomatization and Chiroptical Properties - Aix-Marseille Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2022

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

Abstract

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 ÀCH(OH)CF 3 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-bisspiro-isobenzofuran-anthracenes, when using organic singleelectron transfer oxidants. The chiroptical properties of the alcohols and the corresponding dearomatized products were compared and showed an important modulation of the intensity.
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Dates and versions

hal-03961798 , version 1 (29-01-2023)

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Dorian Sonet, Mattéo Cayla, Raphaël Méreau, Estelle Morvan, Aline Lacoudre, et al.. Chiral Anthranyl Trifluoromethyl Alcohols: Structures, Oxidative Dearomatization and Chiroptical Properties. Chemistry - A European Journal, 2022, 28 (72), pp.e202202695. ⟨10.1002/chem.202202695⟩. ⟨hal-03961798⟩
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