ChemInform Abstract: BRIDGED HELICENES‐ 3,15‐ETHANO‐ AND 3,15‐(2‐OXAPROPANO)‐(7)HELICENE. SYNTHESIS, PROTON NMR SPECTROSCOPY AND X‐RAY DIFFRACTION STUDY

Joly, M.; Defay, Nicole; Martin, Richard; Declerq, J. P.; Germain, Gabriel; Soubrierpayen, B.; Meerssche, M. Van

doi:10.1002/chin.197732216

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“…The shortest C•••C contact is found between C1 and C26 (2.901-2.935 Å) in the inner helix, and these atoms are connected by the subsequent transformation. The centroid distance between the two terminal benzene rings in crystalline F 4 - [7]helicene 2 (3.57-3.70 Å) is shorter than that in crystalline unsubstituted [7]helicene (3.78-3.89 Å) [16][17][18][19][20] , which indicates favourable stacking interactions between the upper F 4 -benzene and the lower unsubstituted benzene moieties at the terminals [21][22][23][24] .…”

Section: Resultsmentioning

confidence: 99%

Triple photochemical domino reaction of a tetrafluorostilbene terminating in double fluorine atom transfer

et al. 2018

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In domino reactions, the product formed in one step undergoes a subsequent transformation under identical reaction conditions. Owing to the spontaneous nature of these reactions, it is difficult to isolate the key intermediates, and these are thus usually presumed. Here we perform a photoinduced domino reaction consisting of three photochemical steps. First, oxidative photocyclisation of a tetrafluorostilbene derivative generates tetrafluoro[7]helicene, which readily undergoes a photoinduced intramolecular Diels-Alder reaction. The resulting product then undergoes a double fluorine atom transfer under the same photochemical conditions. As a result, the four originally adjacent fluorine atoms are separated into two pairs in the final product. One advantage of a photochemical domino process over a thermal one is that the process can be suspended and restarted. Hence, precise control of the irradiation time allows us to isolate the thermally stable intermediates and characterise them using X-ray crystallography, thus confirming the until-now putative domino process.

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Section: Resultsmentioning

confidence: 99%

Triple photochemical domino reaction of a tetrafluorostilbene terminating in double fluorine atom transfer

et al. 2018

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show abstract

ChemInform Abstract: BRIDGED HELICENES‐ 3,15‐ETHANO‐ AND 3,15‐(2‐OXAPROPANO)‐(7)HELICENE. SYNTHESIS, PROTON NMR SPECTROSCOPY AND X‐RAY DIFFRACTION STUDY

Abstract: Ausgehend von den Verbindungen (I) bzw. (IV) werden nach angegebenen Reaktionsfolgen die Phenanthrene (III) und (VI) dargestellt und zu dem Bis‐phenanthryl‐äthylen (VII) kondensiert.

Cited by 1 publication

References 1 publication

Triple photochemical domino reaction of a tetrafluorostilbene terminating in double fluorine atom transfer

Triple photochemical domino reaction of a tetrafluorostilbene terminating in double fluorine atom transfer

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