2019
DOI: 10.1021/acs.joc.9b01871
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Photodecarboxylation of Substituted Naphthylmethyl Arylacetate Esters: Synthesis of Naphthylarylethanes

Abstract: The synthesis of naphthylarylethanes via the photodecarboxylation of naphthylmethyl arylacetate esters is reported where the aryl group is able to stabilize a charge transfer reaction. The reaction proceeds via intramolecular charge transfer from the donor to acceptor, thereby enhancing a pathway to produce, within the solvent cage, the desired diarylethane products. These in-cage naphthylarylethanes are produced in good yields, in a single photochemical step, with the use of cyclohexane as a solvent providing… Show more

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Cited by 2 publications
(1 citation statement)
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“…The emission is situated at ≈430 nm for all compounds, and only a small bathochromic shift of ≈5 nm was observed when the spectra were recorded in an aqueous buffered solution. We have not observed fluorescence that could be associated with the emission of charge-transfer (CT) state, which was postulated as a reactive intermediate in the photolysis of m -hydroxymethylaniline ester derivatives or naphthylalkyl esters . However, a relatively large Stokes shift of ≈7400 cm –1 is in accord with a large stabilization of the emissive state with respect to the Franck–Condon (FC) state in polar solvents.…”
Section: Resultssupporting
confidence: 86%
“…The emission is situated at ≈430 nm for all compounds, and only a small bathochromic shift of ≈5 nm was observed when the spectra were recorded in an aqueous buffered solution. We have not observed fluorescence that could be associated with the emission of charge-transfer (CT) state, which was postulated as a reactive intermediate in the photolysis of m -hydroxymethylaniline ester derivatives or naphthylalkyl esters . However, a relatively large Stokes shift of ≈7400 cm –1 is in accord with a large stabilization of the emissive state with respect to the Franck–Condon (FC) state in polar solvents.…”
Section: Resultssupporting
confidence: 86%